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

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

1
Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O.Box 5003, NO-1432 Ås, Norway
2
Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, NO-0315 Oslo, Norway
*
Author to whom correspondence should be addressed.
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 (CC BY 3.0).

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MDPI and ACS Style

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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