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Total Synthesis of (+)‐Brefeldin C, (+)‐nor‐Me Brefeldin A and (+)‐4‐ epi ‐nor‐Me Brefeldin A
Author(s) -
Archambaud Sylvie,
Legrand Frédéric,
AphecetcheJulienne Karine,
Collet Sylvain,
Guingant André,
Evain M.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901233
Subject(s) - brefeldin a , chemistry , desymmetrization , stereochemistry , lactone , ring (chemistry) , organic chemistry , enantioselective synthesis , biochemistry , catalysis , cell , golgi apparatus
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.