Synthesis of dl-12-epiverticillol

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

Research output: Contribution to journalArticle

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

Fingerprint

Bryophyta
Ships
Boats
Lactones
Ether
Conformations
Catalysts
Cyclohexane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kato, T., Hoshikawa, M., Yaguchi, Y., Izumi, K., Uotsu, Y., & Sakai, K. (2002). Synthesis of dl-12-epiverticillol. Tetrahedron, 58(45), 9213-9222. https://doi.org/10.1016/S0040-4020(02)01192-4

Synthesis of dl-12-epiverticillol. / Kato, Tadahiro; Hoshikawa, Masahiro; Yaguchi, Yoshihiro; Izumi, Kiyokazu; Uotsu, Yukio; Sakai, Ken.

In: Tetrahedron, Vol. 58, No. 45, 04.11.2002, p. 9213-9222.

Research output: Contribution to journalArticle

Kato, T, Hoshikawa, M, Yaguchi, Y, Izumi, K, Uotsu, Y & Sakai, K 2002, 'Synthesis of dl-12-epiverticillol', Tetrahedron, vol. 58, no. 45, pp. 9213-9222. https://doi.org/10.1016/S0040-4020(02)01192-4
Kato T, Hoshikawa M, Yaguchi Y, Izumi K, Uotsu Y, Sakai K. Synthesis of dl-12-epiverticillol. Tetrahedron. 2002 Nov 4;58(45):9213-9222. https://doi.org/10.1016/S0040-4020(02)01192-4
Kato, Tadahiro ; Hoshikawa, Masahiro ; Yaguchi, Yoshihiro ; Izumi, Kiyokazu ; Uotsu, Yukio ; Sakai, Ken. / Synthesis of dl-12-epiverticillol. In: Tetrahedron. 2002 ; Vol. 58, No. 45. pp. 9213-9222.
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