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Molecules 2014, 19(3), 3804-3812; doi:10.3390/molecules19033804
Article

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

1, 1,*  and 2
Received: 31 December 2013 / Revised: 7 March 2014 / Accepted: 10 March 2014 / Published: 24 March 2014
(This article belongs to the Special Issue Fatty Acids)
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Abstract

The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield.
Keywords: Callyspongia sp; polyunsaturated fatty acid; EPA; DHA; iodolactonization; synthesis; marine sponge metabolite Callyspongia sp; polyunsaturated fatty acid; EPA; DHA; iodolactonization; synthesis; marine sponge metabolite
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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Langseter, A.M.; Stenstrøm, Y.; Skattebøl, L. Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.. Molecules 2014, 19, 3804-3812.

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