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Both enantiomers of (3S)-(-)- and (3R)-(+)-Neodictyoprolenol [(3S,5Z,8Z)-(-)-1,5,8-unde-catrien- 3-ol] were successfully converted to the algal sex pheromone, (1S,2R)-(-)-dictyopterene B and (1R,2S)-(+)-dictyopterene B in high enantiomeric purities (e.e. > 99%), respectively, by the biomimetic reaction involving phosphorylation and elimination under a mild condition

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.). This snythetic methods will make it easier to search these compounds in marine algae and to study their biosynthesis.

Chemical structure-odor correlations in the isomers of n-C9-methylene interrupted dienols were explored using synthetic nine isomers of these alcohols. The synthetic dienols were purified by recrystallization or column chromatography of their 3,5-dinitrobenzoate de­ rivatives. Chemical structure-odor correlations in all the isomers of the purified n-nonadien-1-ols were analyzed by treating the data obtained statistically with the principal component analysis method (Sakoda et al., 1995; Cramer et al., 1988) in comparison with those of n-nonen-1-ols. The odor profiles of the n-nonadien-1-ols were attributable largely to the geometries of the isomers, compared with n-nonen -1-ols (Sakoda et al., 1995). With the principal component analysis, the odor profiles of the series of the dienols were successfully integrated into the first and the second principal components. The first component (PC 1) consisted of combined characteristics of fruity, fresh, sweet, herbal and oily-fatty, and the second component (PC 2) leaf or grassy and vegetable-like. Of the methylene interrupted dienol isomers, (2E ,6Z)-and (3Z,6Z)-nonadien-1-ols which are natural products and have (6Z) in the same, deviated markedly from the other isomers as seen in (6Z)-nonen -1-ol of n-nonen-1-ols. That suggests that the double bond of (ω3Z) was an important factor for natural characteristic odor.