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  • Title: Synthesis of the C1-C9 fragment of callipeltoside-A.
    Author: Velázquez F, Olivo HF.
    Journal: Org Lett; 2000 Jun 29; 2(13):1931-3. PubMed ID: 10891194.
    Abstract:
    [reaction: see text] The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.
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