DIISOBUTYLALUMINUM "2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE - NOVEL STEREOSELECTIVE REDUCING AGENT FOR PROSTAGLANDIN SYNTHESIS

被引:75
作者
IGUCHI, S [1 ]
NAKAI, H [1 ]
HAYASHI, M [1 ]
YAMAMOTO, H [1 ]
机构
[1] UNIV HAWAII,DEPT CHEM,HONOLULU,HI 96822
关键词
D O I
10.1021/jo01322a045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In an effort to explore the selective reducing agents suitable for prostaglandin synthesis, diisobutylaluminum 2, 6-di-tert-butyl-4-methylphenoxide (1) is found to be among the best. Reduction of the C-15 ketone 2a with 1 in toluene at -78 °C produced the desired-alcohol 3a in 95% yield with 92% stereoselectivity. The procedure is suitable for the syn-p-phenylbenzoyl ester 2d as the substrate. © 1979, American Chemical Society. All rights reserved.
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页码:1363 / 1364
页数:2
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