Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation

Sho Hirai, Masayuki Utsugi, Mitsuhiro Iwamoto, Masahisa Nakada

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.

Original languageEnglish
Pages (from-to)355-359
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number1
DOIs
Publication statusPublished - 2015 Jan 2

Keywords

  • Cyclization
  • Enantioselectivity
  • Natural products
  • Palladium
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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