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  • Title: Total synthesis of (S)-(-)-(E)-15,16-dihydrominquartynoic acid: a highly potent anticancer agent.
    Author: Gung BW, Kumi G.
    Journal: J Org Chem; 2004 May 14; 69(10):3488-92. PubMed ID: 15132560.
    Abstract:
    The conjugated entriyne natural product, (S)-(E)-15,16-dihydrominquartynoic acid (1), is synthesized in five linear steps and 30% overall yield from the known aldehyde 11. The key step is a one-pot in situ desilylation/Cadiot-Chodkiewicz coupling reaction affording the entriyne unit. The bromoalkyne 6 with an omega-carboxylic acid group was found to undergo a copper-catalyzed cross-coupling reaction producing the desired diyne intermediate 10, while the corresponding omega-ester bromoalkyne 14 failed to couple with triethylsilylacetylene under a variety of conditions.
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