Issue 19, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction

Satoshi Yamauchi,*a   Kenji Takeda,a   Makoto Ganahaa  and  Yoshiro Kinoshitaa  

* Corresponding authors

a College of Agriculture, Ehime University, Tarumi 3-5-7, Matsuyama, Ehime, 790-8566, Japan
E-mail: syamauch@agr.ehime-u.ac.jp
Fax: +81-89-977-4364

Abstract

Novel yeast reduction which gave (1R,2S)-hydroxy ester 10 and (1S,5S)-lactone 11 from racemic ketoester 12 was discovered. After 10 and 11 were converted to lactone 15 and 17, enantiomeric excesses were determined as 99% and 95%, respectively. This novel yeast reduction was applied to synthetic study of metabolites of 5-oxo-ETE 1. (R)-6,7-Dihydro-5-HETE lactone 5 and (S)-6,7-dihydro-5-HETE lactone 6 were synthesized from 15 and 17, respectively.

Graphical abstract: Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction

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Article information

DOI
https://doi.org/10.1039/B206843P
Article type
Paper
Submitted
12 Jul 2002
Accepted
06 Aug 2002
First published
30 Aug 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2156-2160

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Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction

S. Yamauchi, K. Takeda, M. Ganaha and Y. Kinoshita, J. Chem. Soc., Perkin Trans. 1, 2002, 2156 DOI: 10.1039/B206843P

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