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

Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi 753-8515, Japan. Fax: +81-839-33-5849. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 54c, 1027-1032 (1999); received June 7/July 12, 1999 Algae, Enantioselective Synthesis, Neodictyoprolene, Pheromones Neodictyoprolenol [(-)-(5')-(l,5Z,8Z)-undecatrien-3-ol], dictyoprolenol [(-)-(S )-(l,5Z )undecadien-3-ol] and their acetates neodictyoprolene [(+)-(5)-3-acetoxy-(l,5Z,8Z)-undecatriene] and dictyoprolene [(+)-(S)-3-acetoxy-(l,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 (Pseudomonas sp.) and Novozym 435® (Candida sp.). A combination of acylation of the alcohols and hydrol­ ysis of the acetates by Novozym 435® produced neodictyoprolenol, neodictyoprolene, dictyo­ prolenol and dictyoprolene with high optical purities over 99% enantiomeric excess (e.e.). This snythetic methods will make it easier to search these compounds in marine algae and to study their biosynthesis.