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Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers viaη3-allylpalladium intermediates
Mikko Passiniemi,Ari M. P. Koskinen
Organic & Biomolecular Chemistry Pub Date : 01/24/2011 00:00:00 , DOI:10.1039/C0OB00643B
Abstract

A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η3-allylpalladium intermediate.

Graphical abstract: Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers viaη3-allylpalladium intermediates
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