Issue 13, 2021

Palladium catalyzed reductive Heck coupling and its application in total synthesis of (−)-17-nor-excelsinidine

Abstract

Monoterpene indole alkaloids, bearing a highly substituted piperidine ring, are a structurally diverse class of bioactive natural products, found in various parts of the world. Herein, we reported the construction of the key piperidine ring via palladium catalyzed reductive Heck coupling with a good syn selective manner, avoiding the usage of stoichiometric, highly toxic, air sensitive and moisture sensitive Ni(COD)2. To further showcase the value of this methodology, we realized the total synthesis of the structurally unique zwitterionic monoterpene indole alkaloid (−)-17-nor-excelsinidine in 9 steps, in which the key ammonium–acetate connection (N4–C16) of (−)-17-nor-excelsinidine was constructed via oxidative coupling in excellent yield and high regioselectivity under NBS/pyridine from the enolate of geissoschizine.

Graphical abstract: Palladium catalyzed reductive Heck coupling and its application in total synthesis of (−)-17-nor-excelsinidine

Supplementary files

Article information

Article type
Paper
Submitted
02 ม.ค. 2564
Accepted
10 ก.พ. 2564
First published
17 ก.พ. 2564
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 7570-7574

Palladium catalyzed reductive Heck coupling and its application in total synthesis of (−)-17-nor-excelsinidine

L. Yuan, L. Chen, X. Yan, K. Gao and X. Wang, RSC Adv., 2021, 11, 7570 DOI: 10.1039/D1RA00015B

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