Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin |
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Authors: | Daisuke MatsumuraToshimasa Takarabe Takumi TodaTakashi Hayamizu Kiyoto SawamuraKen-ichi Takao Kin-ichi Tadano |
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Affiliation: | Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
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Abstract: | The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described. |
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Keywords: | (+)-Spiculoic acid A (+)-Zyggomphic acid Marine natural product Cytotoxicity Intramolecular reaction Diels-Alder reaction |
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