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

被引:11
|
作者
Yamauchi, S [1 ]
Takeda, K [1 ]
Ganaha, M [1 ]
Kinoshita, Y [1 ]
机构
[1] Ehime Univ, Coll Agr, Matsuyama, Ehime 7908566, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 19期
关键词
D O I
10.1039/b206843p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:2156 / 2160
页数:5
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