Reinvestigation of palladium-catalyzed allylation of the monoacetate of 4-cyclopentene-1,3-diol and synthesis of the coronafacic acid ethyl ester

被引：1

作者：

Kinouchi, Wataru ^{[1
]}

Kosaki, Yusuke ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 51期

关键词：

Palladium; Allylic substitution; 4-Cyclopentene-1,3-diol monoacetate; beta-Keto ester; Coronafacic acid; ASYMMETRIC TOTAL SYNTHESES; (+)-CORONAFACIC ACID; BUILDING-BLOCKS; ALKYLATION; STEREOCHEMISTRY; CONFIGURATION; JASMONATE; QUININE;

D O I：

10.1016/j.tetlet.2013.10.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A larger quantity of a beta-keto ester that is 1.5-1.7 equiv more than the base (t-BuOK, NaH) was found to be essential in securing sufficient yields of the products in the palladium-catalyzed allylic substitution of the monoacetate of 4-cyclopentene-1,3-diol with beta-keto esters. This requirement also works well for substitutions with the TBS ether of the monoacetate and the monoacetate of 2-cyclohexene-1,4-diol. As an application, the coronafacic acid ethyl ester was synthesized as an optically active form. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7017 / 7020

页数：4

共 36 条

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