Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Identifieur interne : 000224 ( Ncbi/Curation ); précédent : 000223; suivant : 000225Toward 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
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