Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

Mitsuhiro Iwamoto, Masayuki Miyano, Masayuki Utsugi, Hatsuo Kawada, Masahisa Nakada

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol™. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.

Original languageEnglish
Pages (from-to)8647-8651
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number47
DOIs
Publication statusPublished - 2004 Nov 15

Keywords

  • Alkylation
  • Carbanion
  • Intramolecular reaction
  • Nucleophilic addition
  • Silicon tethered
  • Taxol™

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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