First total synthesis of a polyunsaturated chromone metabolite isolated from the brown algae Zonaria tournefortii.
Starting from the ethyl ester of eicosapentaenoic acid, the first total synthesis of the marine natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl)chromone has been achieved in six steps and in 14% overall yield.
Anwar
Hany F
HF
School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068 Blindern, N-0316, Oslo, Norway.
Hansen
Trond Vidar
TV
D001547:Benzaldehydes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D015118:Eicosapentaenoic Acid / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D000459:Phaeophyceae / Q000737:chemistry*; D013237:Stereoisomerism
D001547:Benzaldehydes; D001688:Biological Products; D002867:Chromones; C538699:all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl)chromone; D015118:Eicosapentaenoic Acid; C535196:2,4,6-trihydroxybenzaldehyde