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Neodictyoprolenol [(-)-(S)-(1,5Z,8Z)-undecatrien-3-ol], dictyoprolenol [(-)-(S )-(1,5Z)- undecadien-3-ol] and their acetates neodictyoprolene [(+)-(5)-3-acetoxy-(1,5Z,8Z)-undecatriene] and dictyoprolene [(+)-(S)-3-acetoxy-(1,5Z)-undecadiene], which are interesting as possible biosynthetic intermediates of the sex pheromones (dictyopterene B, C′ and D′) of brown algae, were synthesized by chemo-enzymatic methods through optical resolution of racemic neodictyoprolenol and dictyoprolenol using two lipases; Amano PS (Pseudom onas sp.) and Novozym 435 ®  (Candida sp.). A combination of acylation of the alcohols and hydrolysis of the acetates by Novozym 435 ®  produced neodictyoprolenol, neodictyoprolene, dictyoprolenol and dictyoprolene with high optical purities over 99% enantiomeric excess (e.e.).

zeitschrift für naturforschung c

Chemo-Enzymatic Syntheses of Both Enantiomers of Neodictyoprolenol and Neodictyoprolene; Possible Biosynthetic Intermediates of Sex Pheromones in Brown Algae