First efficient synthesis of (±)-erythro-roccellic acid

被引：16

作者：

Mangaleswaran, S ^{[1
]}

Argade, NP ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Synth, Pune 411008, Maharashtra, India

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 15期

关键词：

D O I：

10.1039/b104105n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy, four-step route to (+/-)-erythro-2-dodecyl-3-methylbutanedioic acid (roccellic acid, 9) with 60% overall yield has been described. Wittig reaction of the citraconimide-TPP adduct with dodecanal furnished the mixture of (E)- and (Z)-isomers 3 and 4, which, on base-catalysed exocyclic to endocyclic double bond isomerisation, yielded maleimide 5. Catalytic cis-hydrogenation of 5 using Adam's platinum dioxide catalyst followed by acid-catalysed hydrolysis of formed succinimide 8 gave desired (+/-)-erythro-roccellic acid 9.

引用

页码：1764 / 1766

页数：3

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