title: Highly substituted oxabicyclic derivatives from furan: synthesis of (±)-platensimycin.
abstract: A stereocontrolled approach to a key platensimycin intermediate was achieved from a commercially available furylcarboxylate. Key to our approach is the highly efficient formal [4 + 3] cyclocondensation of a substituted furan with tetrabromocyclopropene along with an intramolecular γ-alkylation to construct the final ring of the caged intermediate.
authors: Department of Pharmaceutical Sciences, University of Connecticut, Storrs, Connecticut 06269, United States.
authors: E Zachary
authors: EZ
authors: Oblak
authors: Dennis L
authors: DL
authors: Wright
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis*; D000478:Alkylation; D062365:Aminobenzoates / Q000138:chemical synthesis*; D000813:Anilides / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D017601:Oxygen Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D017601:Oxygen Compounds; D000218:Adamantane; C510909:platensimycin; C039281:furan