Next Article in Journal
Previous Article in Journal
Molecules 1997, 2(1), 3-6; doi:10.3390/jan97p2
Article

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

, * ,  and
Received: 20 December 1996; Accepted: 10 January 1997 / Published: 29 January 1997
Download PDF [25 KB, uploaded 18 June 2014]
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 Euryspongia rosea; phospholipid fatty acids; stereoselective synthesis; (6Z; 11Z)-octadecadienoic acids; (6Z; 11Z)-eicosadienoic acids; Wittig olefination
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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 BA, Chattopadhyay S, Chattopadhyay A, Mamdapur VR. 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.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert