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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

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Lipids

Abstract

The phospholipid FA composition of the Carbbean 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, 130dimethyltetradecanoic acid, 3,7,11,15-tetramethylhexadecanoic (phytanic) acid, and the 11-methyloctadecanoic acid. In addition, the Δ5,9 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.

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Abbreviations

DME:

dimethoxyethane

DMDS:

dimethyl disulfide

phytanic acid:

3,7,11,15-tetramethylhexadecanoic acid

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Authors and Affiliations

  1. Department of Chemistry, University of Puerto Rico, P.O. Box 23346, 00931-3346, San Juan, Puerto Rico

    Néstor M. Carballeira, Heidyleen Cruz & Norma L. Ayala

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  1. Néstor M. Carballeira
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  2. Heidyleen Cruz
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  3. Norma L. Ayala
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Correspondence to Néstor M. Carballeira.

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Carballeira, N.M., Cruz, H. & Ayala, N.L. Total synthesis of 2-methoxy-14-methylpentadecanoic acid and the novel 2-methoxy-14-methylhexadecanoic acid identified in the sponge agelas dispar . Lipids 37, 1033–1037 (2002). https://doi.org/10.1007/s11745-002-0997-9

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  • DOI: https://doi.org/10.1007/s11745-002-0997-9

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