Synthesis and reactions of polymer-bound Ph3P=C=C=O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates

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 te...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2004-12, Vol.2 (23), p.3524-3529
Main Authors: Schobert, Rainer, Jagusch, Carsten, Melanophy, Claire, Mullen, Gillian
Format: Article
Language:English
Subjects:
Amides - chemistry
Ethers - chemistry
Ketones - chemistry
Molecular Structure
Polymers - chemistry
Spectrum Analysis
Stereoisomerism
Tenuazonic Acid - chemical synthesis
Tenuazonic Acid - chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 alpha-ammonium esters in one step. The mycotoxin (-)-tenuazonic acid was accordingly prepared in just three steps.
ISSN:1477-0520
DOI:10.1039/b412779j