A practical total synthesis of both enantiomers of epoxyquinols A and B

Mitsuru Shoji, Satoshi Kishida, Mitsuhiro Takeda, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

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37 Citations (Scopus)

Abstract

A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.

Original languageEnglish
Pages (from-to)9155-9158
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number50
DOIs
Publication statusPublished - 2002 Dec 9

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Keywords

  • Diels-Alder reaction
  • Epoxyquinols A and B
  • Lipase
  • Resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Shoji, M., Kishida, S., Takeda, M., Kakeya, H., Osada, H., & Hayashi, Y. (2002). A practical total synthesis of both enantiomers of epoxyquinols A and B. Tetrahedron Letters, 43(50), 9155-9158. https://doi.org/10.1016/S0040-4039(02)02271-2