PROSTANOIC ACID CHEMISTRY

被引:115
作者
PIKE, JE
LINCOLN, FH
SCHNEIDE.WP
机构
[1] Experimental Chemistry Unit, Upjohn Company, Kalamazoo, Michigan
关键词
D O I
10.1021/jo01263a071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
General chemical transformations of the prostaglandins are described on a preparative scale, and details are given for the chromatography and isolation of various derivatives of the prostanoic acids. Reductions of 9-oxoand 15-oxoprostaglandins are described leading to both R and S isomers of the corresponding hydroxyls. Dehydration of the 11(β-hydroxy-9-ketoprostanoic acids lead either with acid to the δ10-(PGA) unsaturated ketones or with base to ∆8(12)(PGB) derivatives. 8-Isoprostaglandin E1 obtained as a by-product from preparative biosynthesis can be isomerized under mild basic conditions in high yield to PGE1; sodium borohydride reduction of 8-iso-PGE1 leads to the corresponding two hydroxyl epimers at C-9. Selective protection of both the 9-oxo function and the carboxylic acid is described which allows regeneration of the functional groups under conditions which do not affect the other groups in the molecule. © 1969, American Chemical Society. All rights reserved.
引用
收藏
页码:3552 / &
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