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  • Title: First total synthesis of antimitotic compound, (+)-phomopsidin.
    Author: Suzuki T, Usui K, Miyake Y, Namikoshi M, Nakada M.
    Journal: Org Lett; 2004 Feb 19; 6(4):553-6. PubMed ID: 14961621.
    Abstract:
    [reaction: see text] The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-alpha-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.
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