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  • Title: Asymmetric total synthesis of (-)-amphidinolide V through effective combinations of catalytic transformations.
    Author: Volchkov I, Lee D.
    Journal: J Am Chem Soc; 2013 Apr 10; 135(14):5324-7. PubMed ID: 23514007.
    Abstract:
    An asymmetric total synthesis of (-)-amphidinolide V was accomplished. The synthesis features a base-catalyzed alkynyl silane alcoholysis/ring-closing enyne metathesis sequence for facile construction of a 1,3-diene motif. A diene RCM followed by a ring-contractive allylic transposition of cyclic silyl ethers was incorporated for the stereoselective installation of a functionalized 1,5-diene subunit. An efficient proline-mediated direct cross-aldol condensation of two advanced aldehyde intermediates was utilized for the construction of a key α,β-unsaturated epoxyaldehyde. This total synthesis demonstrates the prowess of metal-catalyzed transformations in complex molecule synthesis.
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