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  • Title: Formal [4+2]-annulation of chiral crotylsilanes: synthesis of the C19-C28 fragment of phorboxazoles.
    Author: Huang H, Panek JS.
    Journal: Org Lett; 2001 May 31; 3(11):1693-6. PubMed ID: 11405688.
    Abstract:
    A stereoselective synthesis of the C19-C28 fragment of phoborxazole A and B is described. The key step is an enantioselective [4 + 2]-annulation of a crotylsilane 10 with a propargylic aldehyde 11 affording a functionalized dihydropyran 12. A solvent-dependent stereoselective epoxidation of dihydropyrans is also documented.
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