A total synthesis of (+)-eremantholide A

Kenichi Takao, Hiroshi Ochiai, Takahiko Hashizuka, Hirokazu Koshimura, Kin ichi Tadano, Seiichiro Ogawa

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate18 and known furanone19 followed by a vinylogous aldol reaction.

Original languageEnglish
Pages (from-to)1487-1490
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number9
DOIs
Publication statusPublished - 1995 Feb 27

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Glucose
3-hydroxybutanal
eremantholide A

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Takao, K., Ochiai, H., Hashizuka, T., Koshimura, H., Tadano, K. I., & Ogawa, S. (1995). A total synthesis of (+)-eremantholide A. Tetrahedron Letters, 36(9), 1487-1490. https://doi.org/10.1016/0040-4039(95)00066-L

A total synthesis of (+)-eremantholide A. / Takao, Kenichi; Ochiai, Hiroshi; Hashizuka, Takahiko; Koshimura, Hirokazu; Tadano, Kin ichi; Ogawa, Seiichiro.

In: Tetrahedron Letters, Vol. 36, No. 9, 27.02.1995, p. 1487-1490.

Research output: Contribution to journalArticle

Takao, K, Ochiai, H, Hashizuka, T, Koshimura, H, Tadano, KI & Ogawa, S 1995, 'A total synthesis of (+)-eremantholide A', Tetrahedron Letters, vol. 36, no. 9, pp. 1487-1490. https://doi.org/10.1016/0040-4039(95)00066-L
Takao K, Ochiai H, Hashizuka T, Koshimura H, Tadano KI, Ogawa S. A total synthesis of (+)-eremantholide A. Tetrahedron Letters. 1995 Feb 27;36(9):1487-1490. https://doi.org/10.1016/0040-4039(95)00066-L
Takao, Kenichi ; Ochiai, Hiroshi ; Hashizuka, Takahiko ; Koshimura, Hirokazu ; Tadano, Kin ichi ; Ogawa, Seiichiro. / A total synthesis of (+)-eremantholide A. In: Tetrahedron Letters. 1995 ; Vol. 36, No. 9. pp. 1487-1490.
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