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

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

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

PII
S30346304S0514749225020062-1
DOI
10.7868/S3034630425020062
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 2
Pages
167-171
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
бициклические γ-лактоны галиеллалактоны бромгидроксилирование галои-минолактонизация (+)-α-метилбензиламин лактон Грико
Date of publication
13.10.2024
Year of publication
2024
Number of purchasers
0
Views
25

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