Synthesis of the C3-C19 segment of phorboxazole B |
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Authors: | Vitale Justin P Wolckenhauer Scott A Do Nga M Rychnovsky Scott D |
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Institution: | Department of Chemistry, University of California--Irvine, 92697-2025, USA. |
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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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