Issue 23, 2004
From the journal:

Organic & Biomolecular Chemistry

Synthesis and reactions of polymer-bound Ph3P[double bond, length as m-dash]C[double bond, length as m-dash]C[double bond, length as m-dash]O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates

Rainer Schobert,*a   Carsten Jagusch,a   Claire Melanophya  and  Gillian Mullena  

* Corresponding authors

a Organic Chemistry Laboratory, University of Bayreuth, Bayreuth, Germany
E-mail: Rainer.Schobert@uni-bayreuth.de
Fax: +49 (0)921 552671

Abstract

Polystyrene-bound cumulated ylide Ph3PCCO was prepared on a large scale in two steps. It reacts with Grignard compounds, amines and alcohols to give immobilized acyl, amide and ester ylides, respectively. Their Wittig reactions lead to alkenes free of phosphane oxide. Optically pure 5-substituted tetramates were obtained from reactions of resin-bound Ph3PCCO with α-ammonium esters in one step. The mycotoxin (−)-tenuazonic acid was accordingly prepared in just three steps.

Graphical abstract: Synthesis and reactions of polymer-bound Ph3P [[double bond, length as m-dash]] C [[double bond, length as m-dash]] C [[double bond, length as m-dash]] O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates

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Article information

DOI
https://doi.org/10.1039/B412779J
Article type
Paper
Submitted
18 Aug 2004
Accepted
30 Sep 2004
First published
05 Nov 2004

Org. Biomol. Chem., 2004,2, 3524-3529

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Synthesis and reactions of polymer-bound Ph3P[double bond, length as m-dash]C[double bond, length as m-dash]C[double bond, length as m-dash]O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates

R. Schobert, C. Jagusch, C. Melanophy and G. Mullen, Org. Biomol. Chem., 2004, 2, 3524 DOI: 10.1039/B412779J

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