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(3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol in the synthesis of insect pheromones with methyl-branched carbon chain and of amphidinolide L C7–C14 fragment

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Abstract

New building block (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol was obtained, and based thereon new formal syntheses of (Z)-trogodermal, a component of the sex pheromone of smaller tea tortrix and of the alarm pheromone of ants of genus Crematogaster were suggested. A new synthetic protocol for (3S)-5-methyl-5-oxopentyl acetate and (3S)-5-(benzyloxy)-3-methylpentanal, convenient building blocks for insect pheromones designing was developed. A new simple and efficient asymmetric synthesis of C7–C14 fragment of the cytotoxic macrolactone amphidinolide L was carried out.

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Authors and Affiliations

  1. Belarusian State University, Minsk, 220030, Belarus

    I. V. Mineeva

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  1. I. V. Mineeva
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Correspondence to I. V. Mineeva.

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Original English Text © I.V. Mineeva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 180–185.

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Mineeva, I.V. (3S,5R)-6-(benzyloxy)-3-methylhexane-1,5-diol in the synthesis of insect pheromones with methyl-branched carbon chain and of amphidinolide L C7–C14 fragment. Russ J Org Chem 50, 168–174 (2014). https://doi.org/10.1134/S1070428014020043

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  • DOI: https://doi.org/10.1134/S1070428014020043

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