Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues

被引：46

作者：

Acharya, HP ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2668501, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 14期

关键词：

aldol reaction; cyclopentenone; palladium; PPAR gamma; Delta(12)-PGJ(2); 15-deoxy-Delta(12,14)-PGJ(2);

D O I：

10.1016/j.tet.2006.01.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (> 95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in > 90% isolated yield was transformed in five steps into the key cyclopentenone possessing the alpha-chain at the gamma position. Aldol reaction of this enone with the w-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al2O3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Delta(12_)PGJ(2) efficiently. Similarly, 15-deoxy-Delta(12,14_)PGJ(2), 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3329 / 3343

页数：15

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