synthesis of key fragments of amphidinolide q — a cytotoxic 12-membered macrolide合成的关键片段amphidinolide问u2014u2014一个细胞毒性由12人组成的大环内酯物.pdfVIP

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synthesis of key fragments of amphidinolide q — a cytotoxic 12-membered macrolide合成的关键片段amphidinolide问u2014u2014一个细胞毒性由12人组成的大环内酯物.pdf

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synthesis of key fragments of amphidinolide q — a cytotoxic 12-membered macrolide合成的关键片段amphidinolide问u2014u2014一个细胞毒性由12人组成的大环内酯物

Molecules 2011, 16, 5422-5436; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide Kohei Kawa, Akihiro Hara, Yuichi Ishikawa and Shigeru Nishiyama * Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan * Author to whom correspondence should be addressed; E-Mail: nisiyama@chem.keio.ac.jp; Tel.: +81 455631717, Fax: +81 455661717. Received: 31 May 2011; in revised form: 20 June 2011 / Accepted: 22 June 2011 / Published: 27 June 2011 Abstract: β-Hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to give the sp2 methyl group. Derivatization of the L-ascorbic acid derivative by Evans asymmetric alkylation and Peterson olefination provided the latter intermediate. The coupling reaction of the segments was examined. Keywords: amphidinolide Q; Amphidinium sp.; macrolide synthesis; cytotoxic marine natural product 1. Introduction Amphidinolide Q (1, Scheme 1) is a member of the cytotoxic macrolide family isolated from the cultured dinoflagellate Amphidinium sp., and its absolute