Total Synthesis of Secobatzelline B

Abstract

A concise and efficient total synthesis of Secobatzelline B is reported. The synthesis involves eight steps starting from known 4,6,7‐trimethoxyindole. Synthetic tactics involve a one‐step reduction of an indole‐3‐glyoxalic ester using LiAlH₄, resulting in complete reduction of the ester group and a partial reduction of the vinylogous amide carbonyl group. Synthesis also involves the use of a mixture of NaCl and oxone as a new reagent for regioselective chlorination of an indoloquinone derivative.

Keywords:

• indoloquinone
• total synthesis
• secobatzelline

Acknowledgments

Authors acknowledge the financial support from the Breast Spore pilot grant from the University of Alabama at Birmingham (UAB). S.V. also acknowledges the financial support from a faculty development grant from UAB Faculty development program (FGDP).