(S)-(+)-可卡因的非对映体全合成及 N-亚磺酰基-β-氨基酯酮的首次可卡因 C-1 类似物合成。

Asymmetric total synthesis of (S)-(+)-cocaine and the first synthesis of cocaine C-1 analogs from N-sulfinyl β-amino ester ketals.

机构信息

Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.

出版信息

Org Lett. 2010 Sep 17;12(18):4118-21. doi: 10.1021/ol1017118.

PMID:20731370

Abstract

Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)(3), undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs.

摘要

亚磺酰亚胺衍生的 α,β-不饱和吡咯烷硝酮，与三异丙氧基铝（Al(O-t-Bu)(3)）加热反应，高度立体选择性地进行分子内环加成，生成三环异噁唑烷，然后经过三步转化得到 C-1 取代的可卡因类似物。