PROSTAGLANDINS AND CONGENERS .20. SYNTHESIS OF PROSTAGLANDINS VIA CONJUGATE ADDITION OF LITHIUM TRANS-1-ALKENYLTRIALKYLALANATE REAGENTS - NOVEL REAGENT FOR CONJUGATE 1,4-ADDITIONS

被引：221

作者：

BERNADY, KF ^{[1
]}

FLOYD, MB ^{[1
]}

POLETTO, JF ^{[1
]}

WEISS, MJ ^{[1
]}

机构：

[1] AMER CYANAMID CO,LEDERLE LABS,METAB DIS RES SECT,PEARL RIVER,NY 10965

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 09期

关键词：

D O I：

10.1021/jo01323a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for effecting 1, 4-conjugate additions to cycloalkenones using trialkyl-irans-1-alkenylalanates is described. The trans-1-alkenyl ligand is selectively transferred in preference to the alkyl ligands, and this transfer is accomplished with retention of double-bond configuration. No 1, 2-addition is observed. The problems raised by the presence of an oxy function in the alkenyl ligand are discussed. By one or the other adaptations of this procedure, dl-11, 15-dideoxyprostaglandin E1, dl-15-deoxyprostaglandin E1, d-lprostaglandin E1, its epimer, their 11-deoxy congeners, and all-rac-15-deoxy-16-hydroxyprostaglandin E2 were synthesized. © 1979, American Chemical Society. All rights reserved.

引用

页码：1438 / 1447

页数：10

共 43 条

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