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  • Title: [4 + 2]-annulations of chiral organosilanes: Application to the total synthesis of leucascandrolide A.
    Author: Su Q, Dakin LA, Panek JS.
    Journal: J Org Chem; 2007 Jan 05; 72(1):2-24. PubMed ID: 17194076.
    Abstract:
    Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesis highlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalized bispyranyl macrolide 3. An efficient assembly and union of the oxazole-containing side chain 4 with macrolide 3 was carried out using a Mitsunobu reaction. A convergent route to the oxazole side chain was developed using a Sonogashira cross-coupling between 2-trifloyloxazole 16 and alkyne 17, which allowed for the installation of the C9'-C10' (Z)-olefin.
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