Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Identifieur interne : 000064 ( Pmc/Checkpoint ); précédent : 000063; suivant : 000065Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Auteurs : Jeffrey A. Gazaille ; Joseph A. Abramite ; Tarek SammakiaSource :
- Organic Letters [ 1523-7060 ] ; 2011.
Abstract
The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19, and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.
Url:
DOI: 10.1021/ol202966m
PubMed: 22149174
PubMed Central: 3272878
Affiliations:
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PMC:3272878Le document en format XML
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<p id="P2">The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19, and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.</p>
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<title-group><article-title>Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction</article-title>
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<contrib-group><contrib contrib-type="author"><name><surname>Gazaille</surname>
<given-names>Jeffrey A.</given-names>
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<contrib contrib-type="author"><name><surname>Abramite</surname>
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<contrib contrib-type="author"><name><surname>Sammakia</surname>
<given-names>Tarek</given-names>
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<xref rid="FN1" ref-type="author-notes">*</xref>
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<aff id="A1">Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215</aff>
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<author-notes><corresp id="FN1"><email>sammakia@colorado.edu</email>
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<p id="P2">The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19, and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.</p>
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<funding-group><award-group><funding-source country="United States">National Institute of General Medical Sciences : NIGMS</funding-source>
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