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  • Title: Synthesis of the C3-C19 segment of phorboxazole B.
    Author: Vitale JP, Wolckenhauer SA, Do NM, Rychnovsky SD.
    Journal: Org Lett; 2005 Jul 21; 7(15):3255-8. PubMed ID: 16018634.
    Abstract:
    [reaction: see text]. Three segment-coupling Prins approaches to the C3-C19 segment of phorboxazole B have been developed. One successful strategy utilized a novel TMSBr-mediated cyclization that proceeded with complete axial selectivity. Displacement of bromide with cesium acetate provided the C13 hydroxyl stereocenter of 22. Additionally, treatment of alpha-acetoxy ether 20 with TFA enabled a more concise synthesis of the C3-C19 target 13 by allowing direct access to the equatorial alcohol.
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