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Updated: Apr 27, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Three-step synthesis of (±)-preussin from decanal
Isac G Rosset1, Rafael M P Dias, Vagner D Pinho
1Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP Brazil.
Abstract:
A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an α,β-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines.
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