Total synthesis of (+)-epoxyquinols A and B

Mitsuru Shoji, Junichiro Yamaguchi, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticle

86 Citations (Scopus)

Abstract

A highly stereoselective HfCl4-mediated Diels-Alder reaction of furan and the chiral acrylate ester of Corey's auxiliary to subsequently give 1, and the realization of the postulated biosynthetic pathway for the construction of epoxyquinols A and B, namely, oxidative 6π electrocyclization, followed by Diels-Alder reaction of the unprotected monomer are the key steps in the asymmetric total synthesis of (+)-epoxyquinols A and B.

Original languageEnglish
Pages (from-to)3192-3194
Number of pages3
JournalAngewandte Chemie - International Edition
Volume41
Issue number17
DOIs
Publication statusPublished - 2002 Sep 2
Externally publishedYes

Fingerprint

Esters
Monomers
Biosynthetic Pathways
epoxyquinol A
epoxyquinol B
furan
acrylic acid

Keywords

  • Asymmetric synthesis
  • Diels-Alder reaction
  • Dimerization
  • Epoxyquinol
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Total synthesis of (+)-epoxyquinols A and B. / Shoji, Mitsuru; Yamaguchi, Junichiro; Kakeya, Hideaki; Osada, Hiroyuki; Hayashi, Yujiro.

In: Angewandte Chemie - International Edition, Vol. 41, No. 17, 02.09.2002, p. 3192-3194.

Research output: Contribution to journalArticle

Shoji, Mitsuru ; Yamaguchi, Junichiro ; Kakeya, Hideaki ; Osada, Hiroyuki ; Hayashi, Yujiro. / Total synthesis of (+)-epoxyquinols A and B. In: Angewandte Chemie - International Edition. 2002 ; Vol. 41, No. 17. pp. 3192-3194.
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