Synthesis of (3 aS ,4 aS ,6 aR )-2-oxo-3,3 a ,4,6 a -tetrahydro-2 H -cyclopenta[b]furan-4-yl acetate, as a key synthon in approaches to (–)-galiellalactone

A. M. Gimazetdinov; Гимазетдинов Айрат Маратович; V. V. Zagitov; Загитов В. В.; Z. R. Makaev; Макаев Зайнутдин Рамилевич; M. S. Miftakhov; Мифтахов М. С.

doi:10.31857/S0514749225020062

Synthesis of (3aS,4aS,6aR)-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl acetate, as a key synthon in approaches to (–)-galiellalactone

Authors: Gimazetdinov A.M.¹, Zagitov V.V.¹, Makaev Z.R.¹, Miftakhov M.S.¹
Affiliations:
1. Ufa Institute of Chemistry UFRS RAS
Issue: Vol 61, No 2 (2025)
Pages: 167-171
Section: Articles
URL: https://hum-ecol.ru/0514-7492/article/view/684320
DOI: https://doi.org/10.31857/S0514749225020062
EDN: https://elibrary.ru/DGQXMT
ID: 684320

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Abstract

The synthesis of bicyclic allyl acetate 2, a promising precursor of (-)-galileolactone 1, is described. The approach is based on the separation of diastereomeric carboxamides obtained by amidation of racemic gem-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. Subsequent steps of transformation of an individual diastereomer include reactions of complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylylation with NBS in aqueous THF, and dehydrobromination.

Keywords

bicyclic γ-lactones, galliellalactones, bromohydroxylation, haloiminolactonization, (+)-α-methylbenzylamine, Grieco lactone

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