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

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 Mar 24;19(3):3804-12. doi: 10.3390/molecules19033804.

Authors

Anne Marie Langseter¹, Yngve Stenstrøm², Lars Skattebøl³

Affiliations

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, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O.Box 5003, NO-1432 Ås, Norway. Yngve.stenstrom@nmbu.no.
³ Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, NO-0315 Oslo, Norway.

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.

MeSH terms

Animals
Biological Products / chemical synthesis*
Lipids / chemical synthesis*
Porifera / chemistry*

Substances

1,6,9,12,15-octadecapenten-3-one
Biological Products
Lipids