Allylation of (R)-2,3-O-Cyclohexylideneglyceraldehyde by 2-Substituted Allyl Stannanes. Application in the Synthesis of Natural Compounds

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Abstract

The possibility of diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with methyl 3-[(tributylstannyl)methyl]but-3-enoate and tributyl[2-(2,2-diethoxyethyl)prop-2-en-1-yl]stannane was studied for the first time. The obtained products were used in the synthesis of valuable building blocks – unsaturated lactones (6R)- and (6S)-6-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2H-pyran-2-one, which found application in the preparation of the C1–C8 fragment of amphidinolides of families C and F, the pheromone of the hemlock moth Lambdina athasaria, in the formal synthesis of the pheromone of the pine moth Lambdina pellucidaria and the coffee leaf miner Leucoptera coffeella.

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Valeria U. Varanchuk

Belarusian State University

Author for correspondence.
Email: i.mineyeva@yandex.ru
ORCID iD: 0009-0009-1118-6916
Belarus, 4, Nezavisimost Ave., Minsk, 220030

Irina V. Mineeva

Institute for Physical Chemical Problems of the Belarusian State University

Email: i.mineyeva@yandex.ru
ORCID iD: 0000-0002-6422-1967
Belarus, 14, Leningradskaya St., Minsk, 220006

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