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A synthesis of brefeldin A

✍ Scribed by R. Baudouy; P. Crabbé; A.E. Greene; C. Le Drian; A.F. Orr

Book ID
104235429
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
220 KB
Volume
18
Category
Article
ISSN
0040-4039

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📜 SIMILAR VOLUMES

A synthesis of (±)-brefeldin A
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A simplified synthesis of (+)-brefeldin
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An effective and enantioselective process for the total synthesis of (+)-brefeldin A (1) is described which start8 from the dextrorotatory ketone 2. Bmfeldin Al (1) has long been known to exhibit an extraordinary range of biological activities including antibiotic, antiviral, cytostatic and antimit

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A formal synthesis of (+)-brefeldin A has been achieved v/a stereoselective construction of hydroxycyclopentane skeleton possessing the requisite hydroxyheptenyl side chain. The highly advanced intermediate 2 has been synthesized from the known Weinreb amide in 19 % overall yield of 11 steps.

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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

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