Preparation and optical resolution of a new helical lactone carrying the 2,8-dioxabicyclo[3.3.0]octane ring system

Makoto Yamaye, Yusuke Ikeda, Namiko Cho, Yoshinori Miura, Tetsutaro Yoshinaga, Katsuya Mukae, Toshiaki Tsuru

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo[3.3.0]octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800Θ (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.

Original languageEnglish
Pages (from-to)137-143
Number of pages7
JournalHeterocycles
Volume63
Issue number1
DOIs
Publication statusPublished - Jan 1 2004

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Glyoxal
Enantiomers
Lactones
Experiments
octane
3,5-xylenol
2,7-dihydroxynaphthalene

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Preparation and optical resolution of a new helical lactone carrying the 2,8-dioxabicyclo[3.3.0]octane ring system. / Yamaye, Makoto; Ikeda, Yusuke; Cho, Namiko; Miura, Yoshinori; Yoshinaga, Tetsutaro; Mukae, Katsuya; Tsuru, Toshiaki.

In: Heterocycles, Vol. 63, No. 1, 01.01.2004, p. 137-143.

Research output: Contribution to journalArticle

Yamaye, Makoto ; Ikeda, Yusuke ; Cho, Namiko ; Miura, Yoshinori ; Yoshinaga, Tetsutaro ; Mukae, Katsuya ; Tsuru, Toshiaki. / Preparation and optical resolution of a new helical lactone carrying the 2,8-dioxabicyclo[3.3.0]octane ring system. In: Heterocycles. 2004 ; Vol. 63, No. 1. pp. 137-143.
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