Synthetic Communications · 1999 · 19 citations · 13 references
Epimer Via Dodec-3-en-11-olideBioorganic ChemistryEngineeringOrganic ChemistryChemistryChemical BiologyDodec-3-en-ll-olide 3Antimicrobial Drug DiscoveryBiochemistryDiversity-oriented SynthesisCucujid Grain BeetlesAntibacterial AgentAntimicrobial CompoundNatural Product SynthesisBiomolecular Engineering12-Membered βγ-Epoxylactones 7Natural SciencesMicrobiologySynthetic Chemistry
Abstract A novel route to dodec-3-en-ll-olide 3, a macrolide pheromone of cucujid grain beetles is reported. Compound 3 provides an access to the antimicrobial (±)-patulolides and (±)-epipatulolide C. Conformational restrictions hamper the rearrangement of the 12-membered βγ-epoxylactones 7 to corresponding allylic alcohols 2.
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Chemoselective addition of organotitanium reagents to carbonyl compounds
Manfred T. Reetz, Jürgen Westermann, Rainer Steinbach et al. · Chemische Berichte · 1985 · 144 citations