A synthetic approach toward taxol analogs: Studies on the construction of the CD ring

Tony K.M. Shing, Chi M. Lee, Ho Y. Lo

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Tricycle 6, containing the CD ring of taxol, is constructed from (S)-(+)-carvone in 21 steps involving a Diels-Alder reaction with isoprene, a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular S N2 reaction as the key steps.

Original languageEnglish
Pages (from-to)9179-9197
Number of pages19
JournalTetrahedron
Volume60
Issue number41
DOIs
Publication statusPublished - 2004 Oct 4

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Keywords

  • Diels-Alder reaction
  • Reduction
  • Taxol analog

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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