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Total Synthesis of 2-methoxy-14-methylpentadecanoic Acid and the Novel 2-methoxy-14-methylhexadecanoic Acid Identified in the Sponge Agelas Dispar

Total Synthesis of 2-methoxy-14-methylpentadecanoic Acid and the Novel 2-methoxy-14-methylhexadecanoic Acid Identified in the Sponge Agelas Dispar

Néstor M Carballeira, Heidyleen Cruz, Norma L Ayala

Lipids. 2002 Nov;37(11):1033-7.

PMID: 12558052

Abstract:

The phospholipid FA composition of the Caribbean sponge Agelas dispar was revisited and 40 different FA were identified. Among these a novel 2-methoxylated FA, namely, the anteiso methyl-branched 2-methoxy-14-methylhexadecanoic acid, was identified together with the recently discovered iso methyl-branched 2-methoxy-14-methylpentadecanoic acid and the normal-chain 2-methoxytetradecanoic acid. The structures of the iso and anteiso methyl-branched 2-methoxylated FA were confirmed by total syntheses, which were accomplished in seven steps and in 45-48% overall yields. Other phospholipid FA identified in A. dispar include the unusual methyl-branched 10,13-dimethyltetradecanoic acid, 3,7,11,15-tetramethylhexadecanoic (phytanic) acid, and the 11-methyloctadecanoic acid. In addition, the delta5,9 FA (5Z,9Z)-15-methyl-5,9-hexadecadienoic acid and (5Z,9Z)-5,9-octadecadienoic acid were characterized. These findings establish alternative FA biosynthetic possibilities for these marine organisms.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP5918296	14-Methylhexadecanoic acid		5918-29-6	Price

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