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  • Title: Stereocontrolled [4+2]-annulation accessing dihydropyrans: synthesis of the C1a-C10 fragment of kendomycin.
    Author: Lowe JT, Panek JS.
    Journal: Org Lett; 2005 Apr 14; 7(8):1529-32. PubMed ID: 15816744.
    Abstract:
    [reaction: see text] Development of new organosilane reagents bearing C-centered chirality where the stereocenter is fully substituted, and their use in the stereocontrolled synthesis of cis- and trans-dihydropyrans containing a trisubstituted olefin is described. The reagents participate in Lewis acid promoted [4+2]-annulations providing useful levels of selectivity with both aliphatic and aromatic aldehydes. A stereoselective synthesis of the C1a-C10 fragment of kendomycin (1) is also described.
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