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

Autor: V. R. Mamdapur, A. Chattopadhyay, S. Chattopadhyay, B. A. Kulkarni
Jazyk: angličtina
Rok vydání: 1997
Předmět:
Zdroj: Molecules, Vol 2, Iss 1, Pp 3-6 (1997)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/jan97p2
Popis: 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.
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