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  • Title: Halichondrin B: synthesis of a C1-C14 model via desymmetrization of (+)-conduritol E.
    Author: Lambert WT, Burke SD.
    Journal: Org Lett; 2003 Feb 20; 5(4):515-8. PubMed ID: 12583757.
    Abstract:
    [reaction: see text] A model C1-C14 segment (1) of halichondrin B was synthesized from (+)-conduritol E (7) in 18 steps and 2.9% overall yield. Key features of the synthesis include the novel ozonolytic desymmetrization of C(2)-symmetric diol 6, the early-stage construction of the C-ring which accompanies installation of the crucial C12 stereocenter, and the use of an enol ether C14-ketone surrogate as a precursor to the CDE-"caged" ketal.
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