Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to a chiral fumarate

TETRAHEDRON LETTERS

卷:54

Article

Hethcox, J. Caleb¹  Shanahan, Charles S.¹  Martin, Stephen F.¹ 

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

关键词: Conjugate addition;    Total synthesis;    Chiral auxiliary;    Butyrolactone;    Succinate;   

DOI  :  10.1016/j.tetlet.2013.02.014

来源: Elsevier

【 摘 要 】

A diastereoselective conjugate addition of a variety of monoorganocuprates, Li[RCuI], to chiral fumarates to provide funtionalized succinates has been developed. The utility of this reaction is demonstrated in a concise total synthesis of (-)-dihydroprotolichesterenic acid that required only four steps and proceeded in an overall 31% yield. (c) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free