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

Anne Marie Langseter; Yngve Stenstrøm; Lars Skattebøl

doi:10.3390/molecules19033804

Molecules (Mar 2014)

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

Anne Marie Langseter,
Yngve Stenstrøm,
Lars Skattebøl

Affiliations

Anne Marie Langseter: Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O.Box 5003, NO-1432 Ås, Norway
Yngve Stenstrøm: Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O.Box 5003, NO-1432 Ås, Norway
Lars Skattebøl: Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, NO-0315 Oslo, Norway

DOI: https://doi.org/10.3390/molecules19033804
Journal volume & issue: Vol. 19, no. 3
pp. 3804 – 3812

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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