Synthesis of Prostaglandin and Phytoprostane B1 Via Regioselective Intermolecular Pauson-Khand Reactions

被引：54
作者：
Vazquez-Romero, Ana
Cardenas, Lydia
Blasi, Emma
Verdaguer, Xavier [1 ]
Riera, Antoni
机构：
[1] Univ Barcelona, URSA PCB, IRB Barcelona, E-08028 Barcelona, Spain
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 14期
关键词：
ETHYLENE EQUIVALENTS; OLEFINATION REACTION; DINOR ISOPROSTANES; VINYL ESTERS; CHEMISTRY; OLIGOMERS; ACIDS;
D O I：
10.1021/ol901213d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach to the synthesis of prostaglandin and phytoprostanes B-1 is described. The key step is an intermolecular Pauson-Khand reaction between a silyl-protected propargyl acetylene and ethylene. This reaction, promoted by NMO in the presence of 4 angstrom molecular sieves, afforded the 3-tert-butyldimethylsilyloxymethyl-2-substituted-cyclopent-2-en-1-ones (III) in good yield and with complete regioselectivity. Deprotection of the silyl ether, followed by Swern oxidation, gave 3-formyl-2-substituted-cyclopent-2-en-1-ones (II). Julia olefination of the aldehydes II with the suitable chiral sulfone enabled preparation of PPB1 type I and PGB(1).
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页码：3104 / 3107
页数：4
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