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Synthetic studies toward verrucosidin: Determination of the absolute configuration

✍ Scribed by Jin K. Cha; R.J. Cooke

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 309 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96757-1

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✦ Synopsis

The tetrahydrofuran portion 3 of verrucosidin I, a potent neurotoxin, is synthesized in an enmtiomerically pure form via the stereoselective osmylation of the chiral hydroxy diene ester 5 as a key step. The stereoselective synthesis of structurally complex tetrahydrofuran units has currently received extensive attention.2 Development of a new methodology for the stereocontrolled construction of highly functional&d tetrahydrofurans poses a considerable synthetic challenge.

From the fungus Penicillium verrucosum var. cyclopiwn, verrucosidin, a potent neurotoxin, was isolated, the structure of which was established to be 1 by chemical, spectroscopic and x-ray crystallographic studies.3p4

Very recently Yamamura and coworkers synthesized its degradation product 2 starting from D-glucose,

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