Email this article Synthesis of (3aS,4S,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
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Affiliations:
- Ufa Institute of Chemistry UFRS RAS
- Issue: Vol 61, No 2 (2025)
- Pages: 167-171
- Section: Articles
- URL: https://journal-vniispk.ru/0514-7492/article/view/304560
- DOI: https://doi.org/10.31857/S0514749225020062
- EDN: https://elibrary.ru/dgqxmt
- ID: 304560
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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.
About the authors
A. M. Gimazetdinov
Ufa Institute of Chemistry UFRS RAS
Email: gimazetdinov@anrb.ru
prosp. Oktyabrya, 71, Ufa, 450054 Russia
V. V. Zagitov
Ufa Institute of Chemistry UFRS RASprosp. Oktyabrya, 71, Ufa, 450054 Russia
Z. R. Makaev
Ufa Institute of Chemistry UFRS RASprosp. Oktyabrya, 71, Ufa, 450054 Russia
M. S. Miftakhov
Ufa Institute of Chemistry UFRS RASprosp. Oktyabrya, 71, Ufa, 450054 Russia
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