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

Seiji Amano, Noriko Ogawa, Masami Ohtsuka, Noritaka Chida

Research output: Contribution to journalArticle

48 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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Immunosuppressive Agents
Derivatives
Glucose
Vanadium
Epoxidation
Sesquiterpenes
Chirality
Epoxy Compounds
Sulfur
Carbon
Alcohols
FR 65814
Cyclohexane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose. / Amano, Seiji; Ogawa, Noriko; Ohtsuka, Masami; Chida, Noritaka.

In: Tetrahedron, Vol. 55, No. 8, 19.02.1999, p. 2205-2224.

Research output: Contribution to journalArticle

Amano, Seiji ; Ogawa, Noriko ; Ohtsuka, Masami ; Chida, Noritaka. / Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose. In: Tetrahedron. 1999 ; Vol. 55, No. 8. pp. 2205-2224.
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