Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive...

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Bibliographic Details
Published in:Organic letters 2004-07, Vol.6 (14), p.2485-2488
Main Authors: Fader, Lee D, Carreira, Erick M
Format: Article
Language:English
Subjects:
Biological Factors - chemical synthesis
Biological Factors - chemistry
Catalysis
Indicators and Reagents
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Stereoisomerism
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Summary:A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0490633