Molecules 2011, 16(7), 5422-5436; doi:10.3390/molecules16075422
Article

Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide

Kohei Kawa, Akihiro Hara, Yuichi Ishikawa and Shigeru Nishiyama* email
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.
Received: 31 May 2011; in revised form: 20 June 2011 / Accepted: 22 June 2011 / Published: 27 June 2011
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Abstract: 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.
Keywords: amphidinolide Q; Amphidinium sp.; macrolide synthesis; cytotoxic marine natural product

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MDPI and ACS Style

Kawa, K.; Hara, A.; Ishikawa, Y.; Nishiyama, S. Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide. Molecules 2011, 16, 5422-5436.

AMA Style

Kawa K, Hara A, Ishikawa Y, Nishiyama S. Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide. Molecules. 2011; 16(7):5422-5436.

Chicago/Turabian Style

Kawa, Kohei; Hara, Akihiro; Ishikawa, Yuichi; Nishiyama, Shigeru. 2011. "Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide." Molecules 16, no. 7: 5422-5436.

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