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A total synthesis of (+)-brefeldin a

✍ Scribed by Takeshi Kitahara; Kenji Mori; Masanao Matsui

Book ID: 104212647
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 282 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)71000-8

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✦ Synopsis

A key intermediate, a substituted cyclopentanonitrile (10) with correct stereochemistry. was prepared from D-mannitol and converted to the Corey's intermexate (27) without a C15-epimer, which was finally transformed to (+)-brefeldin A. (+)-Brefeldin A (l), is;La:ed from a variety of fungi by several groups*, possesses a wide range of biological activity ' , and the complete structure was determined by Sigg et al4 by X-ray analysis. Because of its wide spectrum of activity and macrocyclic structure, brefeldin A has been an attractive target for the synthetic chemist and up to date the total synthesis of (k)-(l) was achieved by three groups5, but none of the synthesis of (+)-brefeldin A itself is accomplished yet.

Here we wish to report the first total synthesis of (+)-brefeldin A.

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