A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone

Akiharu Satake, Isao Shimizu

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The enantioselective synthesis of (8R,8aS)-hcxahydro-8-methyl-5(1H)-indolizinone ((-)-13), which is a synthetic intermediate of 5,8-disubstituted indolizidine alkaloids has been carried out. Reaction of ethyl (E)-(4R, 5R)-8-benzyloxy-4, 5-epoxy-4-methyl-2-octenoate (4) with formic acid in the presence of Pd2(dba)3CHCl3 and n-Bu3P as a catalyst gave ethyl (E)-(4R, 5R)-8-benzyloxy-5-hydroxy-4-methyl-2-octenoate (5), which was converted to (-)-13 in 8 and steps.

Original languageEnglish
Pages (from-to)1405-1408
Number of pages4
JournalTetrahedron: Asymmetry
Volume4
Issue number7
DOIs
Publication statusPublished - 1993

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formic acid
Indolizidines
Alkaloids
alkaloids
Formic acid
catalysts
Catalysts
synthesis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone. / Satake, Akiharu; Shimizu, Isao.

In: Tetrahedron: Asymmetry, Vol. 4, No. 7, 1993, p. 1405-1408.

Research output: Contribution to journalArticle

Satake, Akiharu ; Shimizu, Isao. / A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone. In: Tetrahedron: Asymmetry. 1993 ; Vol. 4, No. 7. pp. 1405-1408.
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