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A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin

✍ Scribed by Hidemi Yoda; Hiroyasu Yamazaki; Kunihiko Takabe

Book ID: 103977392
Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 120 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(96)00009-2

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✦ Synopsis

An efficient and novel process is described for the asymmetric synthesis of (2S, 3S, 5R )-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin employing reductive deoxygenation of a functionalized quaternary ct-hydroxy N-Boc pyrrolidine obtained by stereocontroUed elaboration of tri-O-benzyl-I~-D-arabinofuranose. The synthetic strategy involves no separation of stereoisomers through the entire sequence.

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