巴泽拉定D的不对称全合成。

Asymmetric total synthesis of batzelladine D.

作者信息

Cohen F, Overman L E, Sakata S K

机构信息

Department of Chemistry, University of California, Irvine 92697-2025, USA.

出版信息

Org Lett. 1999 Dec 30;1(13):2169-72. doi: 10.1021/ol991269u.

DOI:10.1021/ol991269u

PMID:10836070

Abstract

[formula: see text] The first enantioselective total synthesis of a batzelladine alkaloid is described. The central reaction in the synthesis of (-)-batzelladine D (2) is a tethered Biginelli condensation of a guanidine aldehyde and an acetoacetic ester to generate a 7-substituted-1-iminohexahydropyrrolo-[1,2-c]pyrimidine intermediate having the anti stereochemistry of the methine hydrogens flanking the pyrrolidine nitrogen.

摘要

[化学式：见正文] 本文描述了一种 batzelladine 生物碱的首次对映选择性全合成。(-)-batzelladine D（2）合成中的关键反应是胍醛与乙酰乙酸乙酯的 tethered Biginelli 缩合反应，生成一种 7-取代-1-亚氨基六氢吡咯并-[1,2-c]嘧啶中间体，该中间体在吡咯烷氮两侧的次甲基氢具有反式立体化学结构。