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Absolute stereochemistry of the strevertenes

✍ Scribed by Jinsong Guo; Gerhard Schlingmann; Guy T. Carter; Koji Nakanishi; Nina Berova

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 252 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:1<43::aid-chir8>3.0.co;2-n

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✦ Synopsis

The CD exciton chirality method was applied to determine the absolute stereochemistry of the strevertenes, antifungal pentaene macrolides produced by Streptoverticillium sp. LL-30F848. The CD difference spectrum of strevertene A methyl ester 15-dimethylaminobenzoate showed a positive couplet between the dimethylaminobenzoate and the pentaene chromophores, and therefore established the 15R configuration. Thus, by considering the relative configurations of the remaining stereogenic centers as derived from X-ray crystallography and ROESY experiments, the absolute stereochemistry of the strevertenes is established as

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