Absolute and relative configuartion of L-660,631

✍ Scribed by M.D. Lewis; R. Menes

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 290 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95609-0

✦ Synopsis

The relative and absolute stereochemistry of the potent antifungal agent L-660,631 has been determined to be 1 by synthesis of an appropriate degradation product.

Triynecarbonate L-664631 (1) isolated from acfirromyceres fermentation broths, is a new broad spectrum antifungal agent active in vitro against pathogenic yeasts and filamentous fungi.' This compound is a potent pre-squalene inhibitor of sterol biosynthesis in Candida albicans.2 Elucidation of the gross structure of this compound has been reported previously.' Triynecarbonate 1 is highly unstable and must be handled only in dilute solutions, as neat preparations polymerize rapidly, often violently, under ambient conditions.

Due to its rather intractable nature, and the difficulty in preparing suitable crystalline derivatives for crystallographic analysis, a synthetic chemical study was undertaken in order to determine the absolute and relative stereochemical configuration of this molecule.