Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Org Lett. 2012 Sep 7;14(17):4338-41. doi: 10.1021/ol301743t. Epub 2012 Aug 13.
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.
报道了 Pigmentosin A、Talaroderxine A 及其非对映异构体 Talaroderxine B 的高效和立体选择性合成。双萘环系统通过钒催化的三环前体的酚偶联组装而成。这些关键中间体是通过保护的 Orsellinate 酯的迈克尔-迪克曼环加成反应制备的，所需的吡喃酮通过 Ghosez 的砜-环氧化物环加成反应的新变体获得。报道了 Pigmentosin 的初步生物实验结果。
