Dideoxyverticillin A

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| ImageFile = 11,11'-Dideoxyverticillin A.svg

| ImageSize = 250px

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| PIN = (3S,3′S,5aR,5′aR,10bR,10′bR,11aS,11′aS)-2,2′,3,3′-Tetramethyl-2,2′,3,3′,5a,5′a,6,6′-octahydro-11H,11′H-[10b,10′b-bi-3,11a-disulfanopyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole]-1,1′,4,4′-tetrone

| OtherNames = 11,11′-Dideoxyverticillin A; 11,11′-Dideoxyverticillin

|Section1={{Chembox Identifiers

| CASNo = 12795-76-5

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BDQ3M208XA

| PubChem = 3084126

| ChemSpiderID = 10477789

| ChEMBL = 2172426

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|Section2={{Chembox Properties

| C=30 | H=28 | N=6 | O=4 | S=4

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Dideoxyverticillin A, also known as (+)-11,11′-dideoxyverticillin A, is a complex epipolythiodioxopiperazine{{Cite journal | title = The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis |vauthors=Gardiner DM, Waring P, Howlett BJ | journal = Microbiology | date = April 2005 | volume = 151 | issue = 4 | pages = 1021–1032 | doi = 10.1099/mic.0.27847-0 | pmid = 15817772| doi-access = free }} initially isolated from the marine fungus Penicillium sp. in 1999.{{cite journal |vauthors=Son BW, Jensen PR, Kauffman CA, Fenical W | title = New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium | journal = Natural Product Letters | volume = 13 | issue = 3 | pages = 213–222 | date= May 1999 | doi = 10.1080/10575639908048788 }} It has also been found in the marine fungus Bionectriaceae,{{cite journal |vauthors=Figueroa M, Graf TN, Ayers S, Adcock AF, Kroll DJ, Yang J, Swanson SM, Munoz-Acuna U, de Blanco EJ, Agrawal R, Wani MC | title = Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae | journal = The Journal of Antibiotics | volume = 65 | issue = 11 | pages = 559–564 | date= November 2012 | pmid = 22968289| doi = 10.1038/ja.2012.69 | pmc=3573876}} and belongs to a class of naturally occurring 2,5-diketopiperazines.{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | date = May 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}}

Dideoxyverticillin A potently inhibits the tyrosine kinase activity of the epidermal growth factor receptor (median inhibitory concentration = 0.14 nM), exhibits antiangiogenic activity, and has efficacy against several cancer cell lines. Its reported anticancer mechanism is that it acts as a farnesyl transferase inhibitor. Dozens of semi-synthetic anticancer compounds have been made from dideoxyverticillin A. Dimeric derivatives are reported to have better anticancer activity.{{cite journal |vauthors=Boyer N, Morrison KC, Kim J, Hergenrother PJ, Movassaghi M | title = Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids | journal = Chemical Science | volume = 4 | issue = 4 | pages = 1646–1657 | date= 2013 | pmid = 23914293 | doi = 10.1039/C3SC50174D | pmc=3728915| url= http://dspace.mit.edu/bitstream/1721.1/95495/1/Movassaghi_Synthesis%20and.pdf }}

The enantioselective first total synthesis of (+)-11,11′-dideoxyverticillin A, the structure of which contains many sterically congested, contiguous stereogenic centers as well as acid- and base-labile and redox-sensitive functionality, was biosynthetically inspired and achieved with high levels of chemical sophistication.{{cite journal |vauthors=Kim J, Ashenhurst JA, Movassaghi M | title = Total synthesis of (+)-11,11'-dideoxyverticillin A | journal = Science | volume = 324 | issue = 5924 | pages = 238–241 | date= April 2009 | pmid = 19359584 | doi = 10.1126/science.1170777 | pmc=4238916}}