Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid

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Molecules 1997, 2(1), 3-6; doi:10.3390/jan97p2

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Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid

B. A. Kulkarni, S. Chattopadhyay * , A. Chattopadhyay and V. R. Mamdapur

Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai - 400 085, India

* Author to whom correspondence should be addressed.

Received: 20 December 1996 / Accepted: 10 January 1997 / Published: 29 January 1997

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Abstract: 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.

Keywords: Euryspongia rosea; phospholipid fatty acids; stereoselective synthesis; (6Z; 11Z)-octadecadienoic acids; (6Z; 11Z)-eicosadienoic acids; Wittig olefination

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MDPI and ACS Style

Kulkarni, B.A.; Chattopadhyay, S.; Chattopadhyay, A.; Mamdapur, V.R. Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid. Molecules 1997, 2, 3-6.

AMA Style

Kulkarni B.A., Chattopadhyay S., Chattopadhyay A., Mamdapur V.R. Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid. Molecules. 1997; 2(1):3-6.

Chicago/Turabian Style

Kulkarni, B. A.; Chattopadhyay, S.; Chattopadhyay, A.; Mamdapur, V. R. 1997. "Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid." Molecules 2, no. 1: 3-6.

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