A convenient C-H functionalization platform for pyrroloiminoquinone alkaloid synthesis

TETRAHEDRON

卷:75

Article

Smith, Myles W.¹  Falk, Isaac D.¹  Ikemoto, Hideya¹  Burns, Noah Z.¹ 

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

关键词: Natural products;    Total synthesis;    C-H functionalization;    Alkaloids;   

DOI  :  10.1016/j.tet.2019.05.009

来源: Elsevier

【 摘 要 】

Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family - and in particular the antitumor discorhabdins - built upon sequential selective C-H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A-C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free