%0 Journal Article
%T Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid
%A B. A. Kulkarni
%A S. Chattopadhyay
%A A. Chattopadhyay
%A V. R. Mamdapur
%J Molecules
%D 1997
%I MDPI AG
%R 10.3390/jan97p2
%X A stereoselective synthesis of (6Z, 11Z)-octadecadienoic acid (1) and (6Z, 11Z)-eicosadienoic acid (2) from easily accessible pentane-1,5-diol (3) is described. Thus, compound 3 on pyranylation and oxidation gave the aldehyde 5 which was converted to the acid 7 by Wittig reaction with a suitable phosphorane. Its depyranylation and oxidation furnished the key aldehyde 9 which upon Wittig reaction with n-heptylidene and n-nonylidene phosphoranes, respectively followed by alkaline hydrolysis afforded the title acids.
%K Euryspongia rosea
%K phospholipid fatty acids
%K stereoselective synthesis
%K (6Z
%K 11Z)-octadecadienoic acids
%K (6Z
%K 11Z)-eicosadienoic acids
%K Wittig olefination
%U http://www.mdpi.com/1420-3049/2/1/3