Synthesis of 6,6'-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B |
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| Authors: | Charles I Grove Michael J Di Maso Firoz A Jaipuri Michelle B Kim Jared T Shaw |
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| Affiliation: | Department of Chemistry, One Shields Avenue, University of California , Davis, California 95616, United States. |
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| Abstract: | Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin. |
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