Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds

被引:31
作者
Acharya, HP [1 ]
Kobayashi, Y [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
Delta(12)-PGJ(2); 15-deoxy-Delta(12,14)-PGJ(2); 4-cyclopentene-1,3-diol monoacetate; palladium catalyst; aldol reaction; cyclopentenone;
D O I
10.1016/j.tetlet.2003.11.143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A key cyclopentenone possessing the alpha-chain was synthesized from TBS ether of 4-cyclopentene-1,3-diol monoacetate, and submitted to aldol reaction at the alpha'-position with the omega-chain aldehydes followed by dehydration to produce the title compounds. In a similar manner, 5-dehydro compounds (acetylene analogues) were synthesized successfully. In addition, palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with methyl malonate, the first step of the synthesis, was improved to afford the product in high yield by using t-BuOK or LDA in place of NaH. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1199 / 1202
页数:4
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