Synthesis of Pyripyropene A

Steven V. Ley; Matthew O’Brien

doi:10.1055/s-0031-1289919

Synfacts, Inhaltsverzeichnis

Synfacts 2012; 8(1): 0003
DOI: 10.1055/s-0031-1289919

Synthesis of Natural Products and Potential Drugs

Synthesis of Pyripyropene A

Rezensent(en):

Steven V. Ley

,

Matthew O’Brien

Abstract

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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

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.

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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