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

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

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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 amphidinolide Q; Amphidinium sp.; macrolide synthesis; cytotoxic marine natural product
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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