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Asymmetric synthesis of (+)-(S)-Massoia lactone, pheromone of Idea leuconoe. Formal total synthesis of valilactone and lachnelluloic acid

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Abstract

Simple and efficient asymmetric synthesis was developed of the cyclic scaffold of (-)-valilactone, an effective inhibitor of the pancreas lipase, applying the Keck allylation in the key stage of building up the carbon skeleton of the target molecule and of the unnatural (S)-isomer of Massoia lactone, lachnelluloic acid, possessing fungicidal properties, and (5R,7S)-7-hydroxy-5-dodecanolid, pheromone component of the Large Tree Nymph butterfly Idea leuconoe.

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Authors and Affiliations

  1. Belarus 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, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1665–1672.

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Mineeva, I.V. Asymmetric synthesis of (+)-(S)-Massoia lactone, pheromone of Idea leuconoe. Formal total synthesis of valilactone and lachnelluloic acid. Russ J Org Chem 49, 1647–1654 (2013). https://doi.org/10.1134/S1070428013110146

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  • DOI: https://doi.org/10.1134/S1070428013110146

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