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Synfacts 2012; 8(1): 0003
DOI: 10.1055/s-0031-1289919
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyripyropene A

Contributor(s):
Steven V. Ley
,
Matthew O’Brien
Odani A, Ishihara K, Ohtawa M, Tomoda H, Omura S, * Nagamitsu T. * Kitasako University, Tokyo, Japan
Total Synthesis of Pyripyropene A.

Tetrahedron 2011;
67: 8195-8203
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Further Information

Publication History

Publication Date:
19 December 2011 (online)

 
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Key words

titanium-mediated radical cyclization - Petersen olefination - pyripyropene A

Significance

Pyripyropene A is a fungal metabolite isolated from Aspergillus fumigatus FO-1289–2501. It is a potent inhibitor of Acyl-CoA:cholesterol-acyltransferase. Several semi-synthetic derivatives show even greater inhibition.


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Comment

Key steps in this synthesis include the titanium-mediated epoxide opening–radical cyclization (A → D) and a Petersen-olefination/epoxide-opening sequence (F → J). A more scalable sequence from D to F involving Me4NHB(OAc)3 as an alternative reducing agent was also reported.


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