A convenient formation of aporphine core via benzyne chemistry: conformational analysis and synthesis of (R)-aporphine

TETRAHEDRON LETTERS

卷:56

Article

Perecim, Givago P.¹  Rodrigues, Alessandro¹  Raminelli, Cristiano¹ 

[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, Brazil

关键词: (R)-Aporphine;    Aporphine core;    Benzyne chemistry;    Conformational analysis;    1D gradient NOE experiment;   

DOI  :  10.1016/j.tetlet.2015.10.083

来源: Elsevier

【 摘 要 】

Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomericallyenriched aporphine alkaloid. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free