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  • Title: Concise and highly stereoselective synthesis of the C20-C26 building block of halichondrins and Eribulin.
    Author: Shan M, Kishi Y.
    Journal: Org Lett; 2012 Jan 20; 14(2):660-3. PubMed ID: 22236198.
    Abstract:
    A concise, stereoselective, and scalable synthesis of the C20-C26 building block of halichondrins and Eribulin is reported. The synthesis relies on three key transformations: regiospecific Ru-catalyzed intramolecular hydrosilylation, highly stereoselective S(N)2' substitution, and selective conversion of a C-Si to C-I bond. It is carried out in a 5-pot/4-workup operation without chromatographic purification, except for filtration through a silica-gel plug, to give the C20-C26 building block (dr > 200:1; ee > 99%) in ca. 60% overall yield from epoxide 1.
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