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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

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

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PII
S30346304S0514749225040039-1
DOI
10.7868/S3034630425040039
Publication type
Article
Status
Published
Authors
V. U. Varanchuk
  • Affiliation: Belarusian State University
I. V. Mineyeva
  • Affiliation:
    Belarusian State University
    Institute for Physical Chemical Problems of the Belarusian State University
Volume/ Edition
Volume 61 / Issue number 4
Pages
372-386
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.
Keywords
диастереоселективное аллилирование амфидинолиды семейств C и F динофлагеллят 2-замещенный аллилстаннан внутримолекулярная оксо-циклизация Михаэля феромон моли болиголова весеннего Lambdina athasaria
Date of publication
15.12.2025
Year of publication
2025
Number of purchasers
0
Views
29

References

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