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

doi:10.3987/COM-03-9919

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

Center of Advanced Instrumental Analysis

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Pages (from-to)	137-143
Number of pages	7
Journal	Heterocycles
Volume	63
Issue number	1
DOIs	https://doi.org/10.3987/COM-03-9919
Publication status	Published - Jan 1 2004

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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AU - Yamaye, Makoto

AU - Ikeda, Yusuke

AU - Cho, Namiko

AU - Miura, Yoshinori

AU - Yoshinaga, Tetsutaro

AU - Mukae, Katsuya

AU - Tsuru, Toshiaki

PY - 2004/1/1

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AB - 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.

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

Abstract

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