Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid

TETRAHEDRON

卷:71

Article

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

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

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

DOI  :  10.1016/j.tet.2015.05.023

来源: Elsevier

【 摘 要 】

Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral gamma-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (-)-dihydroprotolichesterinic acid to date, but several attempts to prepare other succinate-derived natural products, such as pilocarpine and antrodin E, were unsuccessful. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free