ISSN:
1573-9171
Keywords:
(S)- and (R)-3,7-dimethylocta-l,6-dienes
;
(2RS,6R)- and (2RS,6S)-2,6-dimethyloct-l-yl carboxylates, enzymatic hydrolysis
;
porcine pancreatic lipase
;
(R)-2,6-dimethylocta-2,7-dienal, biohydrogenation
;
bakers' yeast
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract All four stereoisomers of 2,6-diniethyloctan-1-ol, the nearest precursors of the title formates, were synthesized in five to eight stages, with configurational purity ranging from 41 to 96 %, employing a stereodivergent scheme based on the partial hydrolysis of two pseudoracernic substrates, (2RS,6R)-2,6-dimethyloct-1-yl formate and (2RS,6S)-2,6-di-methyloct-1-yl acetate, in the presence of porcine pancreatic lipase (PPL). Configurations and diastereomeric compositions of the alcohols thus obtained were determined by correlating the latter with (S,S)-4,8-diniethyldecanal, prepared on the basis of enantioselective biohydrogenation of (R)-2,6-dimetliylocta-2,7-dienal with bakers' yeast, and by comparing the [α]D values of the alcohols with their NMR data and/or with those of their (S)-MTPA derivatives. The attractant potency of stereoisomeric 2,6-diniethyloct-1-yl formates towardsTribolium confusum was found to vary depending on their diastereomeric composition. The configuration at C(6) exerts some influence on the stereoselectivity of the PPL-catalyzed hydrolysis of pseudoracemic 2,6-dimethyloct-1-yl formates.[/p]
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01433762
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