Prostaglandins. V. Synthesis of dl-dihydroprostaglandin E1. and delta 8(12)-dehydroprostaglandin E1.
摘要：
The facile synthesis of the new prostaglandin analogs, dl-Δ8(12)-dehydroprostaglandin E1 (5) and its 15 epimer 6 is described (Chart I) which consists of a Wittig condensation of 3 with 19 to produce 4 followed by the selective reduction of the 15 ketone with borohydride. Hydrogenation of 5 afforded dl-dihydro-PGE1 (7a) and dl-11,15-bisepidihydro-PGE1 (8), while 6 gave rise to dl-15-epidihydro-PGE1 (9) and dl-11-epidihydro-PGE1 (10). Evidence concerning the stereochemical assignments for the above compounds is also presented. In addition, a new procedure for the large-scale preparation of the Wittig reagent, n-hexanoylmethylene triphenylphosphorane (19), is disclosed (Chart III). The key step is chlorination-decarboxylation of 3-oxooctanoic acid (16) to 17.
展开
DOI：
10.1021/jo00976a032
被引量：
年份：
1972
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
