MICROBIAL STEREO-DIFFERENTIATING REDUCTION IN [2.2]METACYCLOPHANE DERIVATIVES

被引:14
作者
NAKAZAKI, M
CHIKAMATSU, H
HIROSE, Y
SHIMIZU, T
机构
[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Toyonaka, Osaka
关键词
D O I
10.1021/jo01321a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Incubation of (±)-l-oxo[2.2]metacyclophane (9) with Rhodotorula rubra gave a mixture of (+)-axial alcohol 10 and (−)-equatorial alcohol 11 both with remarkably high optical purity. The same high stereoselectivity was observed when R. rubra was incubated with l, 10-dioxo[2.2]metacyclophane (12), which was converted into (−)-axial-equatorial diol 14 via (−)-axial ketol 13. R. rubra was also found to reduce (±)-[2.2]metacyclophane-4-aldehyde (20), affording a 13% yield of the (+)-4-hydroxymethyl derivative 21 with 11.7% optical purity. © 1979, American Chemical Society. All rights reserved.
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页码:1043 / 1048
页数:6
相关论文
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