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First Total Synthesis of (+)-Membrine

✍ Scribed by Wirth, Thomas

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 442 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970616

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✦ Synopsis

Abstract

The easily accessible, optically active diselenide 1 is converted into the chiral selenium electrophile 2 and used for oxyselenenylation reactions of alkenes with functionalized nucleophiles. This reaction allows the synthesis of addition products 4, 6 and 10 with the selenium functionality as precursors for an intramolecular radical cyclization. This strategy is applied to the first total synthesis of optically pure (+)‐membrine (13) by a short synthetic sequence.

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