Total Synthesis of (-)-Geissoschizol through Ir-Catalyzed Allylic Amidation as the Key Step

Yu Zheng; Kun Wei; Yu-Rong Yang

doi:10.1021/acs.orglett.7b03133

Total Synthesis of (-)-Geissoschizol through Ir-Catalyzed Allylic Amidation as the Key Step

Org Lett. 2017 Dec 1;19(23):6460-6462. doi: 10.1021/acs.orglett.7b03133. Epub 2017 Nov 2.

Authors

Yu Zheng^{1

2}, Kun Wei¹, Yu-Rong Yang¹

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
² University of Chinese Academy of Sciences , Beijing 100049, China.

PMID: 29095627
DOI: 10.1021/acs.orglett.7b03133

Abstract

The iridium-catalyzed, Zn(OTf)₂ promoted asymmetric allylic amidation of a secondary alcohol derived from tryptamine has been utilized to forge a tetrahydro-β-carboline. Based on this key step, a novel, facile, and enantioselective total synthesis of (-)-geissoschizol was achieved in 10 steps.

Publication types

Research Support, Non-U.S. Gov't