Total Synthesis of (+)‐Brefeldin C, (+)‐nor‐Me Brefeldin A and (+)‐4‐ epi ‐nor‐Me Brefeldin A | Zendy

Archambaud Sylvie | Zendy; Legrand Frédéric | Zendy; AphecetcheJulienne Karine | Zendy; Collet Sylvain | Zendy; Guingant André | Zendy; Evain M. | Zendy

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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

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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