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

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

Organic letters (2012-10-31)
Shen H Tan, Martin G Banwell, Anthony C Willis, Tristan A Reekie
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].

MATERIALS
Product Number
Brand
Product Description

Supelco
Carbazole, VETRANAL®, analytical standard
Sigma-Aldrich
Carbazole, ≥95% (GC)