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■ Synthesis of Lactam Analog of 4-Epi-brefeldin A

Seung-Mann Paek, Seung-Yong Seo, Kyung-Hoon Min, Dong Mok Shin, Young Keun Chung, and Young-Ger Suh*

*The Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Shillim-Dong, San 56-1, Kwanak-Gu, Seoul 151-742, Korea

Abstract

A concise synthetic route to the lactam analog of 4-epi-brefeldin A is described. The key features of the synthesis involve cross metathesis of the bicyclic lactone intermediate and the side chain subunit readily available from an amino acid, and 13-membered macrolactam formation. Unlike the case of synthesis of natural (+)-brefeldin A, the introduction of C4-alcohol into the 13-membered lactam skeleton furnished the opposite configuration, which was confirmed by X-ray crystallographic analysis.