Toward an Efficient Synthesis of Taxane Analogs by Dienyne Ring-Closing Metathesis

An efficient tandem ring-closing dienyne metathesis of dienynes derived from cyclohex-2-enone affords the [5.3.1] carbon framework characteristic of taxanes in a single-step process. Further stereoselective functionalizations of the resulting [5.3.1] carbon framework lead to an advanced intermediate...

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Bibliographic Details
Published in:Organic letters 2008-09, Vol.10 (17), p.3789-3792
Main Authors: Aldegunde, María J, Castedo, Luis, Granja, Juan R
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Alkynes - chemistry
Cyclization
Magnetic Resonance Spectroscopy - methods
Taxoids - chemical synthesis
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Summary:An efficient tandem ring-closing dienyne metathesis of dienynes derived from cyclohex-2-enone affords the [5.3.1] carbon framework characteristic of taxanes in a single-step process. Further stereoselective functionalizations of the resulting [5.3.1] carbon framework lead to an advanced intermediate in a novel synthetic strategy for taxane analogs.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801469h