Issue 6, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Mikko Passiniemia  and  Ari M. P. Koskinen*a  

* Corresponding authors

a Department of Chemistry, School of Chemical Technology, Aalto University, P.O. Box 16100 (Kemistintie 1), Aalto, Finland
E-mail: ari.koskinen@tkk.fi

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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Article information

DOI
https://doi.org/10.1039/C0OB00643B
Article type
Paper
Submitted
30 Aug 2010
Accepted
25 Nov 2010
First published
24 Jan 2011

Org. Biomol. Chem., 2011,9, 1774-1783

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

M. Passiniemi and A. M. P. Koskinen, Org. Biomol. Chem., 2011, 9, 1774 DOI: 10.1039/C0OB00643B

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