A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

Kouji Kuramochi, Seigo Nagata, Hideyoshi Itaya, Yasuaki Matsubara, Takashi Sunoki, Hiromi Uchiro, Ken Ichi Takao, Susumu Kobayashi

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40 Citations (Scopus)

Abstract

The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

Original languageEnglish
Pages (from-to)9743-9758
Number of pages16
JournalTetrahedron
Volume59
Issue number49
DOIs
Publication statusPublished - 2003 Dec 1

Keywords

  • Aldol reaction
  • Epolactaene
  • Epoxylactone
  • TBAF

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Kuramochi, K., Nagata, S., Itaya, H., Matsubara, Y., Sunoki, T., Uchiro, H., Takao, K. I., & Kobayashi, S. (2003). A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy. Tetrahedron, 59(49), 9743-9758. https://doi.org/10.1016/j.tet.2003.09.021