Synlett
DOI: 10.1055/s-0039-1690247
synpacts
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Ye Zhang
,
Lei Zhang
,
This work was partially supported by the National Basic Research Program of China (973 Program) (2014CB849603). We gratefully acknowledge the Beijing municipal government and Tsinghua University for financial support.
Further Information

Publication History

Received: 02 September 2019

Accepted after revision: 18 October 2019

Publication Date:
05 November 2019 (online)

Abstract

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

 
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