✦ LIBER ✦

A simplified synthesis of (+)-brefeldin A

✍ Scribed by E.J. Corey; Philip Carpino

Book ID: 104228590
Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 226 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97297-6

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✦ Synopsis

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 antimitiotic effects. 2 Recently, the underlying reason for such biological activities has been clarified by a number of important discoveries includiig the following: (1) 1 inhibits protein transport in mammalian cell8 from the endoplasmic reticulum (ER) to the golgi complex (GC)3 and causes disassembly of the GC; (2) 1 inhibit8 sialation, fucosylation, and sulfation of glycoproteins as well as transport of proteins;4 (3) 1 inhibits exocytosis and the presentation of viral proteins to cytotoxic T lymphocytes. 5 These are remarkable action8 for such a small molecule.

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