Synthesis of the key component for preparation of 6-keto-prostaglandins by a two-component coupling process: Synthesis of 6-keto-prostaglandin E(1), ornoprostil and Delta(2)-trans-6-keto-prostaglandin E(1)

被引：6

作者：

Kawanaka, Y ^{[1
]}

Ono, N ^{[1
]}

Yoshida, Y ^{[1
]}

Okamoto, S ^{[1
]}

Sato, F ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT BIOMOLEC ENGN,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 07期

关键词：

D O I：

10.1039/p19960000715

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4- siloxycyclopentanone-2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3 . OEt(2), Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE(1), ornoprostil and Delta(2)-trans-6-keto-PGE(1) by using 1 is also described.

引用

页码：715 / 718

页数：4

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