A convergent approach to batzelladine alkaloids. Total syntheses of (+)-batzelladine E, (-)-dehydrobatzelladine C, and (+)-batzelladine K

TETRAHEDRON

卷:74

Article; Proceedings Paper

Economou, Christos¹  Romaire, Justin P.¹  Scott, Tony Z.¹  Parr, Brendan T.¹  Herzon, Seth B.^1,2 

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Yale Sch Med, Dept Pharmacol, New Haven, CT 06520 USA

关键词: Total synthesis;    Alkaloid;    Tropane;    Batzelladine;    Dehydrobatzelladine;   

DOI  :  10.1016/j.tet.2018.04.050

来源: Elsevier

【 摘 要 】

We recently reported a convergent strategy to access the polycyclic guanidinium alkaloid (+)-batzelladine B via an aldol addition retro-aldol aza-Michael addition cascade. Here we describe the application of this approach toward the total syntheses of (+)-batzelladine E, (-)-dehydrobatzelladine C, and (+)-batzelladine K. The identification of suitable methods to functionalize a common tropane core by electrophilic alkynylation and nucleophilic 1,2-addition were essential to generalizing this approach. We provide evidence for the intermediacy of an acylallene species in the cascade reaction. (C) 2018 Published by Elsevier Ltd.

【 授权许可】

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