Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates

Research output: Contribution to journalJournal articleResearchpeer-review

M. Özlügedik, Jesper Langgaard Kristensen, J. Reuber, R. Fröhlich, D. Hoppe

Stereoselective addition of aldehydes 4 to metallated 1-(1-cycloalkenyl) methyl N,N-diisopropylcarbamates 1 gave cyclic homoaldol adducts 6. By applying the (-)-sparteine method, enantiomerically enriched products were obtained. These were oxidatively cyclized to diastereomerically pure ¿-lactones 8 via the ¿-lactol ethers 7. After deprotonation of ¿-lactones 8 with lithium hexamethyldisilazide, a further substitution was achieved. By trapping the lactone enolates 11 with ß-naphthylmethyl bromide, single diastereomers of ¿-lactones 12 were produced.
Original languageEnglish
JournalSynthesis
Issue number14
Pages (from-to)2303-2316
Number of pages14
ISSN0039-7881
DOIs
Publication statusPublished - 1 Oct 2004

ID: 45438453