Synthesis of dl-12-epiverticillol

Tadahiro Kato, Masahiro Hoshikawa, Yoshihiro Yaguchi, Kiyokazu Izumi, Yukio Uotsu, Ken Sakai

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

The first synthesis of 12-epiverticillol 2, a constituent of a moss, Jackiella javanica, was elaborated in a dl-form by setting up 10-cyanoverticillene 3 as a key intermediate. The C1-C2 bond of the intermediate 3 is forced to take axial orientation as in the case of the verticillol. 10-cyanoverticillene 3 was converted to γ-lactone 11, the cyclohexane ring of which was disclosed to take a boat conformation. Decarbonylation was achieved by application of Wilkinson's catalyst to formyl MOM ether 25 derived from 11, and final deprotection furnished the objective 2.

Original languageEnglish
Pages (from-to)9213-9222
Number of pages10
JournalTetrahedron
Volume58
Issue number45
DOIs
Publication statusPublished - Nov 4 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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