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  • Title: Synthesis of the bis-spiroacetal core of the antimitotic agent spirastrellolide B.
    Author: Chen JL, Brimble MA.
    Journal: J Org Chem; 2011 Nov 18; 76(22):9417-28. PubMed ID: 21995770.
    Abstract:
    The spirastrellolides are a family of potent antimitotic agents isolated from the marine sponge Spirastrella coccinea . Synthetic studies toward the DEF bis-spiroacetal core of spirastrellolide B are reported. A modular approach was pursued by the use of two dithiane disconnections to enable a highly convergent synthesis. The ease of lithiation and nucleophilicity of these 2-substituted-1,3-dithianes were investigated during the course of the synthesis, and the alkylations were found to proceed most efficiently at elevated temperatures. Formation of the [5,6,6]-bis-spiroacetal ring system was achieved via a double dithiane deprotection/spiroacetalization strategy.
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