%0 Journal Article
%T Synthesis of Key Fragments of Amphidinolide Q ¡ª A Cytotoxic 12-membered Macrolide
%A Kohei Kawa
%A Akihiro Hara
%A Yuichi Ishikawa
%A Shigeru Nishiyama
%J Molecules
%D 2011
%I MDPI AG
%R 10.3390/molecules16075422
%X b-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.
%K amphidinolide Q
%K Amphidinium sp.
%K macrolide synthesis
%K cytotoxic marine natural product
%U http://www.mdpi.com/1420-3049/16/7/5422