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Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-epi-nor-Me Brefeldin A

✍ Scribed by Sylvie Archambaud; Frédéric Legrand; Karine Aphecetche-Julienne; Sylvain Collet; André Guingant; M. Evain

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
582 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A total synthesis of (+)‐brefeldin C (BFC) and two brefeldin A (BFA) analogues – (+)‐nor‐Me BFA and (+)‐4‐epi‐nor‐Me BFA – has been developed. Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki–Miyaura cross‐coupling reaction to create the C11–C12 bond and a Yamaguchi reaction to form the 13‐membered lactone ring.

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