Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the Aspidosperma alkaloids (±)-limaspermidine and (±)-1-acetylaspidoalbidine

Shen H Tan; Martin G Banwell; Anthony C Willis; Tristan A Reekie

doi:10.1021/ol3026846

Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the Aspidosperma alkaloids (±)-limaspermidine and (±)-1-acetylaspidoalbidine

Org Lett. 2012 Nov 16;14(22):5621-3. doi: 10.1021/ol3026846. Epub 2012 Oct 30.

Authors

Shen H Tan¹, Martin G Banwell, Anthony C Willis, Tristan A Reekie

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.

PMID: 23106356
DOI: 10.1021/ol3026846

Abstract

The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].

Publication types

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

MeSH terms

Aspidosperma / chemistry*
Carbazoles
Chemistry, Organic / methods*
Cobalt / chemistry*
Cyclization
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Nitriles / chemistry
Plant Bark / chemistry
Stereoisomerism
Venezuela

Substances

1-acetylaspidoalbidine
Carbazoles
Indole Alkaloids
Nitriles
limaspermidine
carbazole
Cobalt