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New approach to the synthesis of macrocyclic core of cytotoxic lactone (+)-neopeltolide. Synthesis of C7–C14 segment basing on cyclopropanol intermediates

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Abstract

A new retrosynthetic procedure was developed for the synthesis of the macrocyclic core of a cytotoxic lactone (+)-neopeltolide utilizing cyclopropanol intermediates. The synthesis was suggested and carried out of the C7–C16 segment of (+)-neopeltolide to obtain (4S,6S)-6-[(2S)-2-hydroxypentyl]-4-methyltetrahydro-2H-pyran-2-one. The possibility was demonstrated of a formal synthesis based on the obtained product of the potential antitumor pharmaceutical (+)-neopeltolide.

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

    I. V. Mineeva

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  1. I. V. Mineeva
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Original Russian Text © I.V. Mineeva, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1083–1092.

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Mineeva, I.V. New approach to the synthesis of macrocyclic core of cytotoxic lactone (+)-neopeltolide. Synthesis of C7–C14 segment basing on cyclopropanol intermediates. Russ J Org Chem 51, 1061–1070 (2015). https://doi.org/10.1134/S1070428015080023

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  • DOI: https://doi.org/10.1134/S1070428015080023

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