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Asymmetric syntheses of the lactone core of tetrahydrolipstatin and tetrahydroesterastin and of the oriental hornet Vespa Orientalis pheromone

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Abstract

A synthetic approach to the lactone core of the anti-obesity drugs tetrahydrolipstatin and tetrahydroesterastin has been developed starting from readily accessible methyl (5S)-5-{[tert-butyl(dimethyl)silyl]-oxy}-3-oxohexadecanoate. (6S)-6-Undecyltetrahydro-2H-pyran-2-one, the oriental hornet Vespa Orientalis pheromone, has also been synthesized. A formal synthesis of (3S,4R,6S)-dihydroxy-6-undecyltetrahydro-2H-pyran-2-one (metabolite of a fungus separated from mangrove seeds) has been proposed.

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  1. Belarusian State University, pr. Nezavisimosti 4, Minsk, 220030, Belarus

    I. V. Mineeva

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Original Russian Text © I.V. Mineeva, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 6, pp. 859–865.

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Mineeva, I.V. Asymmetric syntheses of the lactone core of tetrahydrolipstatin and tetrahydroesterastin and of the oriental hornet Vespa Orientalis pheromone. Russ J Org Chem 51, 842–848 (2015). https://doi.org/10.1134/S1070428015060044

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