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, Kenichi Takao, Susumu Kobayashi

Research output: Contribution to journalArticle

39 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

Fingerprint

Lactones
Aldehydes
Anions
epolactaene
3-hydroxybutanal

Keywords

  • Aldol reaction
  • Epolactaene
  • Epoxylactone
  • TBAF

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kuramochi, K., Nagata, S., Itaya, H., Matsubara, Y., Sunoki, T., Uchiro, H., ... 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

A convergent total synthesis of epolactaene : An application of the bridgehead oxiranyl anion strategy. / Kuramochi, Kouji; Nagata, Seigo; Itaya, Hideyoshi; Matsubara, Yasuaki; Sunoki, Takashi; Uchiro, Hiromi; Takao, Kenichi; Kobayashi, Susumu.

In: Tetrahedron, Vol. 59, No. 49, 01.12.2003, p. 9743-9758.

Research output: Contribution to journalArticle

Kuramochi, K, Nagata, S, Itaya, H, Matsubara, Y, Sunoki, T, Uchiro, H, Takao, K & Kobayashi, S 2003, 'A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy', Tetrahedron, vol. 59, no. 49, pp. 9743-9758. https://doi.org/10.1016/j.tet.2003.09.021
Kuramochi K, Nagata S, Itaya H, Matsubara Y, Sunoki T, Uchiro H et al. A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy. Tetrahedron. 2003 Dec 1;59(49):9743-9758. https://doi.org/10.1016/j.tet.2003.09.021
Kuramochi, Kouji ; Nagata, Seigo ; Itaya, Hideyoshi ; Matsubara, Yasuaki ; Sunoki, Takashi ; Uchiro, Hiromi ; Takao, Kenichi ; Kobayashi, Susumu. / A convergent total synthesis of epolactaene : An application of the bridgehead oxiranyl anion strategy. In: Tetrahedron. 2003 ; Vol. 59, No. 49. pp. 9743-9758.
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