Allylation of (R)-2,3-O-Cyclohexylidene glyceraldehyde 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-cyclohexylidene glyceraldehyde 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 C’–C’ 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.

About the authors

V. U. Varanchuk

Belarusian State University

Minsk, Belarus

I. V. Mineyeva

Belarusian State University; Institute for Physical Chemical Problems of the Belarusian State University

Email: i.mineyeva@yandex.ru
Minsk, Belarus; Minsk, Belarus

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