Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

Hiroko Akao, Hiromasa Kiyota, Takao Nakajima, Takeshi Kitahara

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield.

Original languageEnglish
Pages (from-to)7757-7770
Number of pages14
JournalTetrahedron
Volume55
Issue number25
DOIs
Publication statusPublished - Jun 18 1999
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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