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Total Synthesis of (−)-Basiliskamide B

✍ Scribed by Luiz C. Dias; Caroline da Costa S. Gonçalves

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 213 KB
Volume: 350
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200700589

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✦ Synopsis

Abstract

The total synthesis of the polyketide antibiotic (−)‐basiliskamide B is described. The convergent asymmetric synthesis relies on the use of a diastereoselective ethyl ketone aldol reaction followed by a syn selective reduction of a β‐hydroxy ketone and a Stille cross‐coupling between a Z‐vinylstannane and an E‐vinyl iodide to establish the (Z,E)‐dienamide moiety.

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