The formal total synthesis of (+/-)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition

M J Eichberg; R L Dorta; K Lamottke; K P Vollhardt

doi:10.1021/ol006131m

The formal total synthesis of (+/-)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition

Org Lett. 2000 Aug 10;2(16):2479-81. doi: 10.1021/ol006131m.

Authors

M J Eichberg¹, R L Dorta, K Lamottke, K P Vollhardt

Affiliation

¹ Department of Chemistry, University of California at Berkeley, and the Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720-1460, USA. eichberg@socrates.berkeley.edu

PMID: 10956526
DOI: 10.1021/ol006131m

Abstract

A short, highly convergent total synthesis of racemic isostrychnine, and thus strychnine, has been completed. The route involves 14 steps in the longest linear sequence and is highlighted by a cobalt-mediated [2 + 2 + 2]cycloaddition of an alkynylindole nucleus to acetylene.

Publication types

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

MeSH terms

Cobalt
Indicators and Reagents
Models, Molecular
Molecular Conformation
Molecular Structure
Stereoisomerism
Strychnine / chemical synthesis*
Strychnine / chemistry

Substances

Indicators and Reagents
Cobalt
Strychnine