A short and enantioselective preparation of taxol A-ring fragment

Sho Hirai, Naoko Urushizako, Masayuki Miyano, Tomohiro Fujii, Masahisa Nakada

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Two short preparations of the taxol A-ring fragment are described: one via organocatalyzed α-aminoxylation and the other via Sharpless asymmetric dihydroxylation (SAD). The former approach affords the A-ring fragment in 10 steps, and the latter approach involves eight steps to afford the new A-ring fragment in 91% ee, which is made enantiomerically pure through recrystallization. The new A-ring fragment bearing a bromoalkene is confirmed to be useful to form the carbocyclic eight-membered ring of a taxol model compound by palladium-catalyzed intramolecular alkenylation. The preparation of the new A-ring fragment will be beneficial for the total synthesis of taxol as well as other natural products.

Original languageEnglish
Pages (from-to)1888-1892
Number of pages5
JournalTetrahedron Letters
Volume54
Issue number14
DOIs
Publication statusPublished - 2013 Apr 3

Keywords

  • Dihydroxylation
  • Enantioselective
  • Organocatalysis
  • Stereoselective
  • Taxol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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