Synthesis of the putative structure of (±)-amarbellisine

Dandan Liu; Jingbo Chen; Long Ai; Hongbin Zhang; Jianping Liu

doi:10.1021/ol3034093

Synthesis of the putative structure of (±)-amarbellisine

Org Lett. 2013 Jan 18;15(2):410-3. doi: 10.1021/ol3034093. Epub 2012 Dec 28.

Authors

Dandan Liu¹, Jingbo Chen, Long Ai, Hongbin Zhang, Jianping Liu

Affiliation

¹ Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.

PMID: 23273098
DOI: 10.1021/ol3034093

Abstract

The title compound was synthesized mainly by palladium catalytic coupling, cyclopropyl ring-opening rearrangement, epoxidation, Swern oxidation, demethanol reactions, and selective reduction. This synthesis was achieved in 16 steps with 9.7% overall yield. Unfortunately, the published spectroscopic data do not match with those of our synthetic compound.

Publication types

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

MeSH terms

Amaryllidaceae Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids / chemistry
Catalysis
Molecular Structure
Oxidation-Reduction
Palladium / chemistry
Phenanthridines / chemical synthesis*
Phenanthridines / chemistry
Stereoisomerism

Substances

Amaryllidaceae Alkaloids
Phenanthridines
amarbellisine
Palladium