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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