Add time:07/17/2019         Source:sciencedirect.com

Recent developments in the total synthesis of bioactive marine fatty acids are described. For the purpose of this review marine fatty acids have been divided into three main groups, namely methylated, methoxylated, and diunsaturated fatty acids. Within the methylated fatty acids the Wittig coupling of methylketones has been the principal synthetic strategy used to introduce the methyl ramification, while allylic methylation has been achieved through the α-methylation of carbonyls. Vinylic methylated fatty acids, on the other hand, for the most part have been synthesized stereospecifically, using as the key step either a Claisen orthoester rearrangement or a stabilized phosphorane, both methodologies favoring the E isomer. α-Methoxylated marine fatty acids were synthesized via the methylation of the corresponding α-hydroxy acids, which were prepared using Mukaiyama's trimethylsilyl cyanide addition to aldehydes. In addition, some optically active methoxylated fatty acids have been made through the regiospecific ring opening of optically active oxiranes with lithioalkynes. Most recent work with diunsaturated marine fatty acids has been concentrated on the synthesis of Δ5,9 fatty acids. The key strategy has been to use either acetylenic coupling or the selective ring opening of one of the double bonds of (lZ,5Z)-l,5-cyclooctadiene to generate the 9 double bond, followed by Wittig coupling to generate the Δ5 double bond.

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