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  • Title: Synthesis and [4 + 2]-annulation of enantioenriched (z)-crotylsilanes: preparation of the C1-C13 fragment of bistramide A.
    Author: Lowe JT, Panek JS.
    Journal: Org Lett; 2005 Jul 21; 7(15):3231-4. PubMed ID: 16018628.
    Abstract:
    [reaction: see text]. New chiral crotylsilanes that bear a (Z)-olefin geometry were synthesized in high enantiopurity. The reagents participate in [4 + 2]-annulations with aldehydes to give stereochemically complementary pyrans (relative to (E)-crotylsilanes) bearing 2,6-cis-5,6-cis and 2,6-trans-5,6-cis relationships of peripheral functionalities. A stereoselective synthesis of the C1-C13 fragment of bistramide A is also described highlighting this annulation strategy.
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