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Total synthesis of (+)-discodermolide: an improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 beta-ketophosphonate fragment.

Authors
  • Paterson, Ian
  • Lyothier, Isabelle
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Dec 23, 2004
Volume
6
Issue
26
Pages
4933–4936
Identifiers
PMID: 15606103
Source
Medline
License
Unknown

Abstract

[structure: see text] An improved, third-generation, total synthesis of (+)-discodermolide, a potent microtubule-stabilizing anticancer agent of marine sponge origin, is achieved in 11.1% yield over 21 steps. Key steps include a Still-Gennari HWE olefination, performed using NaH as the base, between C1-C8 beta-ketophosphonate 7 and C9-C24 aldehyde 8, introducing the (8Z)-alkene with 10:1 selectivity, and K-Selectride reduction of the derived enone 16, installing the (7S)-configuration.

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