Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose

Seiji Amano, Noriko Ogawa, Masami Ohtsuka, Noritaka Chida

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47 Citations (Scopus)

Abstract

The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

Original languageEnglish
Pages (from-to)2205-2224
Number of pages20
JournalTetrahedron
Volume55
Issue number8
DOIs
Publication statusPublished - 1999 Feb 19

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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