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

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

Research output: Contribution to journalArticle

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
Externally publishedYes

Fingerprint

Enantiomers
Cycloaddition Reaction
Chromatography
Lipase
Derivatives
Kinetics
epoxyquinol A
epoxyquinol B
acryloyl chloride
furan

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

A practical total synthesis of both enantiomers of epoxyquinols A and B. / Shoji, Mitsuru; Kishida, Satoshi; Takeda, Mitsuhiro; Kakeya, Hideaki; Osada, Hiroyuki; Hayashi, Yujiro.

In: Tetrahedron Letters, Vol. 43, No. 50, 09.12.2002, p. 9155-9158.

Research output: Contribution to journalArticle

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, vol. 43, no. 50, pp. 9155-9158. https://doi.org/10.1016/S0040-4039(02)02271-2
Shoji M, Kishida S, Takeda M, Kakeya H, Osada H, Hayashi Y. A practical total synthesis of both enantiomers of epoxyquinols A and B. Tetrahedron Letters. 2002 Dec 9;43(50):9155-9158. https://doi.org/10.1016/S0040-4039(02)02271-2
Shoji, Mitsuru ; Kishida, Satoshi ; Takeda, Mitsuhiro ; Kakeya, Hideaki ; Osada, Hiroyuki ; Hayashi, Yujiro. / A practical total synthesis of both enantiomers of epoxyquinols A and B. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 50. pp. 9155-9158.
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