:Taxodone

Taxodone was first isolated in 1968 from the seeds of Taxodium distichum (Bald Cypress) by S. Morris Kupchan and coworkers. They reported the structure determination and basic chemistry of taxodone and its oxidized rearrangement product, taxodione.{{cite journal |author1=Kupchan, S. M. |author2=Karim, A |author3=Marcks, C. | title = Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum | journal = J. Org. Chem. | year = 1969| volume = 34 | pages = 3912–3918 | issue = 12 | doi = 10.1021/jo01264a036|pmid=5357534 }}{{cite journal |author1=Hanson, R. C. |author2=Lardy, H. A. |author3=Kupchan, S. M. | title = Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors | journal = Science | year = 1970| volume = 168 | pages = 378–380| issue = 3929|doi=10.1126/science.168.3929.378|pmid=4244949 |bibcode=1970Sci...168..378H |s2cid=86616738 }} Taxodone occurs naturally in the form of (+)-taxodone.

Taxodone and/or taxodione have been identified in several plants besides Taxodium distichum including: Rosmarinus officinalis (Rosemary),{{cite journal | author = El-Lakany, Abdalla M.| title = Chlorosmaridione; A Novel Chlorinated Diterpene Quinone Methide from Rosemarinus officinalis L | journal = Natural Product Sciences | year = 2004| volume = 10 | issue = 2 | pages = 59–62}} Salvia barrelieri, Metasequoia glyptostroboides (Dawn Redwood), Salvia munzii (San Diego Sage),{{cite journal |author1=Luis, J. G. |author2=Grillo, T. A. | title = New diterpenes from Salvia munzii: chemical and biogenetic aspects |journal = Tetrahedron | year = 1993| volume = 49| pages = 6277–6284 | doi = 10.1016/S0040-4020(01)87965-5 | issue = 28}} Salvia moorcroftiana,{{cite journal |author1=Simoes, F. |author2=Michavila, A. |author3=Rodriguez, B. |author4=Garcia Alvarez, M. C. |author5=Mashooda, H. | journal = Phytochemistry | year = 1986| volume = 25| pages = 755–756 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3|bibcode=1986PChem..25..755S }} Salvia staminea,{{cite journal | author = Gulacti Topcu1, Esra N. Altiner, Seyda Gozcu, Belkis Halfon, Zeynep Aydogmus, J. M. Pezzuto, Bing-Nan Zhou, David G. I. Kingston| title = Studies on Di- and Triterpenoids from Salvia staminea with Cytotoxic Activity | journal = Planta Med. | year = 2003| volume = 69| issue = 5 | pages = 464–467 | doi = 10.1055/s-2003-39705| pmid = 12802732 | s2cid = 260280222 }} Salvia clevelandii (Cleveland Sage),{{cite journal |author1=Iván C. Guerrero |author2=Lucía S. Andrés |author3=Leticia G. León |author4=Rubén P. Machín |author5=José M. Padrón |author6=Javier G. Luis |author7=José Delgadillo |name-list-style=amp | title = Abietane Diterpenoids from Salvia pachyphylla and S. clevelandii with Cytotoxic Activity against Human Cancer Cell Lines| journal = J. Nat. Prod. | year = 2006| volume = 69| pages = 1803–1805| issue = 12 | doi = 10.1021/np060279i | pmid=17190465}} Salvia hypargeia, Salvia broussonetii,{{cite journal |author1=M. Fraga |author2=Carmen E. Díaz |author3=Ana Guadaño |author4=Azucena González-Coloma |name-list-style=amp | title = Diterpenes from Salvia broussonetii Transformed Roots and Their Insecticidal Activity| journal = J. Agric. Food Chem. | year = 2005| volume = 53| pages = 5200–5206| issue = 13 | doi = 10.1021/jf058045c|pmid=15969497 |bibcode=2005JAFC...53.5200F }} Salvia montbretii,{{cite journal |author1=Ayhan Ulubelen |author-link1 = Ayhan Ulubelen|author2=Gülaçti Topcu | title = New Abietane Diterpenoids from Salvia montbretii| journal = J. Nat. Prod. | year = 1996| volume = 55 | issue = 4 | pages = 441–444 | doi=10.1021/np50082a006}}{{cite journal |author1=Ayhan Ulubelen |author-link1=Ayhan Ulubelen |author2=Gülaçti Topcu | title = Abietane and Rearranged Abietane Diterpenes from Salvia montbretii | journal = J. Nat. Prod. | year = 1996| volume = 59 | issue = 8 | pages = 734–737 | doi = 10.1021/np9602224}} Salvia nipponica,{{cite journal |author1=Ikeshiro Y. |author2=Mase I. |author3=Tomita Y. | title = Abietane-Type Diterpene Quinones from Salvia nipponica | journal = Planta Med. | year = 1991| volume = 57 | issue = 6 | pages = 588 | doi = 10.1055/s-2006-960219|pmid=17226213 |s2cid=36064314 }}{{cite journal | author = Hsiu-Hui Chana, Tsong-Long Hwangb, Chung-Ren Sua, Mopur Vijaya Bhaskar Reddya and Tian-Shung Wu | title = Anti-inflammatory, anticholinesterase and antioxidative constituents from the roots and the leaves of Salvia nipponica Miq. var. formosana | journal = Phytomedicine | year = 2011| volume = 18 | issue = 2–3 | pages = 148–150 | doi = 10.1016/j.phymed.2010.06.017| pmid = 21115331 }} Salvia verbenaca (Wild Clary),{{cite journal | author = A. Kabouche, Z. Kabouche, R. Touzani and C. Bruneau| title = Diterpenes and sterols from the roots of Salvia verbenaca subsp. clandestina | journal = Chemistry of Natural Compounds | year = 2008| volume = 44 | issue = 6 | pages = 824–825 | doi = 10.1007/s10600-009-9204-6| bibcode = 2008CNatC..44..824K | s2cid = 28852886 }} Salvia lanigera,{{cite journal |author1=Ik-Soo Lee |author2=Norito Kaneda |author3=Rutt Suttisri |author4=Abdalla M. El-Lakany |author5=Nawal Sabri |author6=A. Douglas Kinghorn |name-list-style=amp | title = New Orthoquinones from the Roots of Salvia lanigera | journal = Planta Med. | year = 1998| volume = 64 | pages = 632–634 | doi = 10.1055/s-2006-957536 |pmid=17253304 | issue = 7|s2cid=260249066 }}{{cite journal | author = Sabri, N. N., Abou-Donia, A. A., Assad, A. M., Ghazy, N. M., El-lakany, A. M., Tempesta, M. S. and Sanson D. R.| title = Abietane diterpene quinones from the roots of Salvia verbenaca and S. lanigera| journal = Planta Medica | year = 1989| volume = 55| pages = 582 | doi = 10.1055/s-2006-962111 | pmid = 17262492| issue = 6| s2cid = 10020492}} Salvia prionitis,{{cite journal |author1=Li M. |author2=Zhang J. S. |author3=Ye Y. M. |author4=Fang J. N. | title = Constituents of the roots of Salvia prionitis | journal = J Nat Prod | year = 2000 | volume = 63| issue = 1| pages = 139–141 | doi = 10.1021/np990357k|pmid=10650097 }} Salvia deserta,{{cite journal |author1=Y. Tezuka |author2=R. Kasimu |author3=J. X. Li |author4=P. Basnet |author5=K. Tanaka |author6=T. Namba |author7=S. Kadot | title = Constituents of Roots of Salvia deserta SCHANG. (Xinjiang-Danshen)| journal = Chem Pharm Bull | year = 1998| volume = 46| issue = 1 | pages = 107–112 | doi=10.1248/cpb.46.107|doi-access=free }} Salvia phlomoides,{{cite journal | author = Benjamın Rodrıguez| title = A Methoxyabietane Diterpenoid from the Root of Salvia phlomoides and Structural Correction of Another Diterpene from Cryptomeria japonica| journal = Z. Naturforsch. | year = 2003| volume = 58b| pages = 324–327}}{{cite journal |author1=J. A. Hueso-Rodrıguez |author2=M. L. Jimeno |author3=B. Rodrıguez |author4=G. Savona |author5=M. Bruno | title = Abietane diterpenoids from the root of Salvia phlomoides | journal = Phytochemistry | year = 1983| volume = 22| pages = 2005–2009 | doi = 10.1016/0031-9422(83)80033-8 | issue = 9|bibcode=1983PChem..22.2005H }} and Plectranthus hereroensis{{cite journal | author = Olga Batista, M. Fátima Simões, José Nascimento, Sofia Riberio, Aida Duartea, Benjamín Rodríguez and Maria C. de la Torreb | title = A rearranged abietane diterpenoid from Plectranthus hereroensis | journal = Phytochemistry | year = 1996| volume = 41 | issue = 2 | pages = 571–573 | doi = 10.1016/0031-9422(95)00646-X| pmid = 8821435 | bibcode = 1996PChem..41..571B }}

Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers.{{cite journal |author1=A. Otto |author2=H. Walther |author3=W. Püttmann | title = Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany | journal = Organic Geochemistry | year = 1997 | volume = 26| pages = 105–115 | issue = 1–2 | doi = 10.1016/S0146-6380(96)00133-7|bibcode=1997OrGeo..26..105O }}{{cite journal |author1=A. Otto |author2=H. Walther |author3=W. Püttmann | title = Molecular composition of a leaf- and root-bearing Oligocene Oxbow Lake Clay in the Weisselster Basin, Germany | journal = Organic Geochemistry | year = 1994| volume = 22| pages = 275–286 | issue = 2 | doi = 10.1016/0146-6380(94)90174-0|bibcode=1994OrGeo..22..275O }}{{cite journal |author1=Angelika Otto |author2=Bernd R. T. Simoneit |author3=William C. Rember | title = Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia flora, Emerald Creek, Idaho, USA, and from related extant species | journal = Review of Palaeobotany and Palynology | year = 2003| volume = 126 | pages = 225–241 | doi = 10.1016/S0034-6667(03)00088-5 | issue = 3–4|bibcode=2003RPaPa.126..225O }}{{cite journal |author1=Maya Stefanova |author2=Bernd R.T. Simoneit | title = Polar aromatic biomarkers of Miocene-aged Chukurovo resinite and correlation with a progenitor macrofossil | journal = International Journal of Coal Geology | year = 2008 | volume = 75| issue = 3 | pages = 166–174 | doi = 10.1016/j.coal.2008.05.003|bibcode=2008IJCG...75..166S }}{{cite journal |author1=A. Zdravkov |author2=A. Bechtel |author3=R. F. Sachsenhofer |author4=J. Kortenski |author5=R. Gratzer | title = Vegetation differences and diagenetic changes between two Bulgarian lignite deposits – Insights from coal petrology and biomarker composition| journal = Organic Geochemistry | year = 2011| volume = 42 | issue = 3| pages = 237–254 | doi = 10.1016/j.orggeochem.2010.12.006|bibcode=2011OrGeo..42..237Z }}{{cite journal |author1=Yann Hautevelle |author2=Raymond Michels |author3=Fabrice Malartre |author4=Alain Trouiller | title = Vascular plant biomarkers as proxies for palaeoflora and palaeoclimatic changes at the Dogger/Malm transition of the Paris Basin (France)| journal = Organic Geochemistry | year = 2006| volume = 37| issue = 5 | pages = 610–625 | doi = 10.1016/j.orggeochem.2005.12.010|bibcode=2006OrGeo..37..610H }}{{cite journal|author1=Kenneth E. Peters |author2=Clifford C. Walters |author3=J. Michael Moldowan | title = The Biomarker Guide: Biomarkers and isotopes in petroleum systems and Earth History| year = 2005| volume = 2 | pages = 546}}

Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in Salvia texana (Texas Sage).{{cite journal |author1=Gonzalez, A. G. |author2=Aguilar, Z. E. |author3=Luis, J. G |author4=Ravelo, A. G. |author5=Dominguez, X. | title = Quinone methide diterpenoids from the roots of Salvia texana | journal = Phytochemistry | year = 1988| volume = 27|issue=6 | pages = 1777–1781 | doi=10.1016/0031-9422(88)80442-4|bibcode=1988PChem..27.1777G }} 5,6-Didehydro-7-hydroxy-taxodone was found in Salvia munzii. 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in Salvia montbretti.

Taxodone and taxodione possess in vivo activity against Walker intramuscular carcinosarcoma 256 in rats (25 and 40 mg/kg, respectively) and in vitro activity against cells derived from human carcinoma of the nasopharynx (KB) (ED₅₀ = 0.6 and 3 ug/ml respectively). Taxodone and taxodione exhibit antifungal activity against wood decay fungi, with taxodione being especially active against Trametes versicolor and Fomitopsis palustris. Taxodione exhibited the highest antioxidant activity among the tested diterpenoids from the roots of Salvia barrelieri. Taxodone showed potent antibacterial effects against foodborne pathogenic bacteria, such as Listeria monocytogenes ATCC 19166, Salmonella typhimurium KCTC 2515, Salmonella enteritidis KCTC 2021, Escherichia coli ATCC 8739, Escherichia coli O157:H7 ATCC 43888, Enterobacter aerogenes KCTC 2190, Staphylococcus aureus ATCC 6538 and Staphylococcus aureus KCTC 1916 Taxodone showed potent termicidal activity against the subterranean termite, Reticulitermes speratus Kolbe. Taxodione depresses neuronal GABAA receptor-operated Cl-current (IGABA).{{cite journal |author1=D. Rutherford |author2=M. Nielsen |author3=N. Tokutomi |author4=N. Akaike | title = Effects of plant diterpenes on the neuronal GABAA receptor-operated chloride current | journal = NeuroReport | year = 1994| volume = 5| pages = 2569–2572 | doi = 10.1097/00001756-199412000-00041 | issue = 18|pmid=7696606 }} Taxodione may have potential in treatment of cardiovascular disease.{{cite journal |author1=C. R. Tirapelli |author2=S. R. Ambrosio |author3=F. B. da Costa |author4=A. M. de Oliveira | title = Diterpenes: a therapeutic promise for cardiovascular diseases | journal =Recent Patents on Cardiovascular Drug Discovery| year = 2008 | volume = 3|issue=1 | pages = 1–8 | doi = 10.2174/157489008783331689|pmid=18221123 }}

The use of taxodone and taxodione to inhibit hair growth has been patented.[http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5824665 US Patent 5824665][http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6218435 US Patent 6218435][http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=20070203240 US Patent 20070203240] Treatment of benign prostate enlargement with taxodone has also been patented.[http://worldwide.espacenet.com/publicationDetails/originalDocument?CC=WO&NR=2004064736A2&KC=A2&FT=D&date=20040805&DB=EPODOC&locale=en_gb World Patent 2004064736]

Taxodone was the first isolated example of a quinone methide{{cite journal |author1=Karantsios, D. |author2=Scarpa, J. S. |author3=Eugster, C. H. | journal = Helv. Chim. Acta | year = 1966| volume = 49| pages = 1151–1172 | doi = 10.1002/hlca.19660490313 | title = Struktur von Fuerstion | issue = 3}}{{cite journal |author1=Gonzalez, A. G. |author2=Fraga, B. M. |author3=Gonzalez, C. M. |journal = Tetrahedron | year = 1983| volume = 84 |issue=29 | pages = 3033–3036 | doi = 10.1016/s0040-4039(00)88088-0 |title=X-ray analysis of netzahualcoyone, a triterpene Quinone methide from orthosphenia mexicana}}{{cite journal | author = Simoes, F.; Miehavila, A; Rodriguez. B.; Garcia A1varez, M. C.; Mashooda, H.| journal = Phytochemistry | year = 1986| volume = 25| pages = 755–756 | doi = 10.1016/0031-9422(86)88043-8 | title = A quinone methide diterpenoid from the root of Salvia moorciuftiana | issue = 3| bibcode = 1986PChem..25..755S }}{{cite journal |author1=Sankaram, A. V. B. |author2=Murthi, M. M. |author3=Bhaskaraiah, K. |author4=Narasimha Rao, G. L. |author5=Suhrahmanyam, M. |author6=Shoolery, J. N. | journal = Tetrahedron Lett. | year = 1988| volume = 29| pages = 245–248 | doi = 10.1016/S0040-4039(00)80066-0 | title = Bharangin, a novel diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 2}}{{cite journal |author1=Fernando, H. C. |author2=Gunatilaka, A. A. L. |author3=Kumar, V. |author4=Weexatunga, G. | journal = Tetrahedron Lett. | year = 1988| volume = 29| pages = 387–390 | doi = 10.1016/S0040-4039(00)80104-5 | title = Two new quinone-methides from cassine balae: Revised structure of balaenonol | issue = 3}}{{cite journal |author1=Sankaram, A. V. B. |author2=Bhaskaraiah, K. |author3=Marthandamurthi. M. |author4=Subrahmanyam, M. | journal = Tetrahedron Lett. | year = 1989| volume = 30| pages = 867–868 | doi = 10.1016/S0040-4039(01)80638-9 | title = Isobharangin, a new biogenetically significant diterpenoid quinonemethide from pygmacopremna herbacea (Roxb.) moldenke | issue = 7}} with a labile hydrogen adjacent to this reactive chromophore. Kupchan demonstrated that taxodone aromatizes to a catechol ketone upon exposure to mild acid. Air oxidation of this catechol ketone affords taxodione.

400px

Taxodone rearranges easily in the presence of mild acids and reacts readily with nucleophiles. Although taxodone shows higher anticancer and antibacterial activity than taxodione it eluded creation in the laboratory for over 25 years because of its inherent instability. During this time several different groups reported syntheses of the more stable taxodione.{{cite journal |author1=Mori, K. |author2=Matsui, M. | title = Diterpenoid total synthesis. XIII Taxodione, a quinone methide tumor inhibitor |journal = Tetrahedron | year = 1970| volume = 26| pages = 3467–3473 | doi = 10.1016/S0040-4020(01)92926-6 | issue = 14|pmid=5449327 }}{{cite journal |author1=Matsumoto, T. |author2=Tachibana, Y. |author3=Uchida, J. |author4=Fukui, K. | journal = Bull. Chem. Soc. Jpn. | year = 1971| volume = 44| pages = 2766–2770 | doi = 10.1246/bcsj.44.2766 | title = The Total Synthesis of (±)-Taxodione, A Tumor Inhibitor | issue = 10| doi-access = free }}{{cite journal |author1=Matsumoto, T. |author2=Ohsuga, Y. |author3=Fukui, K. | title = Synthesis of Taxodione and Methyl 11-hydroxy-12-methoxy-7-oxobieta-8,11,13-trien-18-oate| journal = Chem. Lett. |volume=3 |issue=3 | year = 1974| pages = 297–300|doi=10.1246/cl.1974.297 }}{{cite journal |author1=Matsumoto, T. |author2=Osbuga, Y. |author3=Harada, S. |author4=Fukui, K. | journal = Bull. Chem. Soc. Jpn. | year = 1977| volume = 50| pages = 266–272 | doi = 10.1246/bcsj.50.266 | title = Synthesis of Taxodione, Royleanone, Cryptojaponol, and Methyl 11-Hydroxy-12-methoxy-7-oxoabieta-8,11)13-trien-18-oate| doi-access = free }}{{cite journal |author1=Matsumoto. T. |author2=Usui, S. |author3=Morimoto. T. | journal = Bull. Chem. Soc. Jpn. | year = 1977| volume = 50| pages = 1575–1579 | doi = 10.1246/bcsj.50.1575 | title = A Convenient Synthesis of (±)-Taxodione, (±)-Ferruginol, and (±)-Sugiol | issue = 6| doi-access = free }}{{cite journal |author1=Ohtsuka, Y. |author2=Tahara, A. | title = Diterpenoids. XLVI. Syntheses of Taxodione, Royleanone and Their Analogues | journal = Chem. Pharm. Bull. | year = 1978| volume = 26|issue=7 | pages = 2007–2013 | doi=10.1248/cpb.26.2007| doi-access = free }}{{cite journal |author1=Snitman, D. L. |author2=Himmelsbach, R. J. |author3=Haltiwanger, R. C. |author4=Watt, D. S. | title = A synthesis of (±)-cryptojaponol and (±)-taxodione | journal = Tetrahedron Lett. | year = 1979| volume = 20|issue=27 | pages = 2477–2480|doi=10.1016/S0040-4039(01)86325-5}}{{cite journal |author1=Johnson, W. S. |author2=Shenvi, A. B. |author3=Boots, S. G. |journal = Tetrahedron | year = 1982| volume = 38| pages = 1397–1404 | doi = 10.1016/0040-4020(82)80219-6 | title = An approach to taxodione involving biomimetic polyene cyclization methodology | issue = 10}}{{cite journal |author1=Stevens, R. V. |author2=Bisaochi, G. G. | journal = J. Org. Chem. | year = 1982| volume = 47| pages = 2396–2399 | doi = 10.1021/jo00133a032 | title = Benzocyclobutenones as synthons for the synthesis of C-11 oxygenated diterpenoids. Application to the total synthesis of (.+-.)-taxodione | issue = 12}}{{cite journal |author1=Poirier, D. |author2=Jean, M. |author3=Burnell, R. H. | title = Alternate Syntheses of Taxodione | journal = Synth. Commun. | year = 1983| volume = 13| pages = 201–205 | doi = 10.1080/00397918308065989 | issue = 3}}{{cite journal |author1=Banerjee, A K |author2=Carrasco, M. C. | title = Synthetic Approaches to (±)-Taxodione | journal = Synth. Commun. | year = 1988| volume = 13|issue=4 | pages = 281–287 | doi=10.1080/00397918308066977}}{{cite journal |author1=Banerjee, A. K |author2=Carrasco, M. C. | journal = J. Chem. Soc., Perkin Trans. 1 | year = 1986| pages = 25–31 | doi = 10.1039/p19860000025 | title = Total synthesis of (±)-12-methoxyabieta-8,11,13-trien-6-one, a versatile intermediate for diterpene syntheses}}{{cite journal |author1=Burnell, P. H. |author2=Jean, M. |author3=Poirer, D. | title = Synthesis of taxodione | journal = Can. J. Chem. | year = 1987| volume = 65| pages = 775–781 | doi = 10.1139/v87-132 | issue = 4}}{{cite journal |author1=Engler, T. A. |author2=Sampath. U. |author3=N aganathan, S. |author4=Van Der Velde, D. |author5=Takusagawa, F. | journal = J. Org. Chem. | year = 1989| volume = 54| pages = 5712–5727 | doi = 10.1021/jo00285a018 | title = A new general synthetic approach to diterpenes: Application to syntheses of (.+-.)-taxodione and (.+-.)-royleanone | issue = 24}}{{cite journal |author1=Haslinger, E. |author2=Michl, G. | journal = Tetrahedron Lett. | year = 1988| volume = 29| pages = 5751–5754 | doi = 10.1016/S0040-4039(00)82181-4 | title = Synthesis of (+)-taxodione from (−)-abietic acid | issue = 45}}{{cite journal |author1=Haslinger, E. |author2=Michl, G. | journal = Justus Liebigs Ann. Chem. |volume=1989 |issue=7 | year = 1989| pages = 677–686|title=missing|doi=10.1002/jlac.198919890212 }}{{cite journal |author1=Harring, S. R |author2=Livinghouse, T. | title = A concise biomimetic total synthesis of (±)-taxodione via a BF₃·MeNO₂ promoted cationic cascade annulation | journal = J. Chem. Soc., Chem. Commun. |issue=6 | year = 1992 | pages = 502–503|doi=10.1039/C39920000502 }}{{cite journal |author1=Ruedi, P. |author2=Eugster, C. H. | journal = Helv. Chim. Acta | year = 1981|volume = 64| pages = 2219–2226 | doi = 10.1002/hlca.19810640728 | title = 14-Hydroxytaxodion: Partialsynthese und Reaktionen | issue = 7}}{{cite journal |author1=Matsumoto, T. |author2=Kawashima, H. |author3=Iyo, K. | journal = Bull. Chem. Soc. Jpn. | year = 1982| volume = 55|pages = 1168–1173 | doi = 10.1246/bcsj.55.1168 | title = Synthesis of 3.BETA.-hydroxytaxodione and coleons S and T | issue = 4| doi-access = free }}

In 1993 taxodone was synthesized for the first time in a 16 step sequence utilizing a unique phenol benzylic epoxide electron reorganization in the final step.{{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = The First Total Synthesis of (±)-Taxodone| journal = Synlett | year = 1994| pages = 335–336 | doi=10.1055/s-1994-22844 | volume=1994|issue=5 |s2cid=196814605 }}{{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = J. Org. Chem. | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }} As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well.

400px

Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.{{cite journal |author1=Scott R. Harring |author2=Tom Livinghouse |name-list-style=amp | title = Polyene cascade cyclizations mediated by BF₃·CH₃NO₂. an unusually efficient method for the direct, stereospecific synthesis of polycyclic intermediates via cationic initiation at non-functionalized 3° alkenes. An application to the total synthesis of (±)-taxodione |journal = Tetrahedron | year = 1994 | volume = 50 | issue = 31 | pages = 9229–9254 | doi = 10.1016/S0040-4020(01)85502-2}}{{cite journal | author = E. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda, M. Lachkar and I. Messouri| title = First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid | journal = Tetrahedron Lett. | year = 2007| volume = 48 | issue = 6 | pages = 989–992 | doi = 10.1016/j.tetlet.2006.12.009}}

• Taxodium distichum
• Quinone methide
• Diterpenoid
• Salvia

{{reflist}}

• [https://www.thieme-connect.com/ejournals/abstract/synlett/doi/10.1055/s-1994-22844 The First Total Synthesis of (±)-Taxodone ]
• {{cite journal |author1=Sanchez, Anthony J. |author2=Konopelski, Joseph P. | title = Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone| journal = J. Org. Chem. | year = 1994| volume = 59| pages = 5445–5452| issue = 18 | doi = 10.1021/jo00097a057 }}
• [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=275528&loc=ec_rcs Taxodone, Pubchem entry]
• [https://books.google.com/books?id=J4DZ_wun8yYC&q=taxodone&pg=PA291 Quinone methides, Steven Edward Rokit]
• [http://www.sciencedirect.com/science/article/pii/000927979390117H Biological and toxicological consequences of quinone methide formation]
• [http://www.iupac.org/publications/pac/pdf/1970/pdf/2102x0227.pdf Recent Advances in the Chemistry of Terpenoid Tumor Inhibitors]

Category:Quinone methides

Category:Tertiary alcohols

Category:Diterpenes

Category:Phenanthrenes

Category:Enols

Category:Secondary alcohols

Category:Diols

Category:Isopropyl compounds

Category:Hydroxyketones