title: Synthesis of Substituted Tetralins and Benzosuberans via BF3·OEt2-Mediated Formal (4 + 2) and (5 + 2) Stereocontrolled Cycloaddition of 4-Alkenols with Veratrol.
abstract: BF3·OEt2-mediated one-pot formal (4 + 2) and (5 + 2) stereocontrolled cycloaddition of 4-alkenols 3 and 4 with veratrol affords the respective substituted tetralins 5 and benzosuberans 6 in good yields. The cascade protocol combines a facile double Friedel-Crafts benzannulation of 4-alkenols 3 and 4 (having two electrophilic sites) and veratrol (7a) (having two nucleophilic sites). A plausible mechanism was studied and proposed.
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , Kaohsiung 807, Taiwan.
authors.forename: Meng-Yang
authors.initials: MY
authors.lastname: Chang
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , Kaohsiung 807, Taiwan.
authors.forename: Yu-Chieh
authors.initials: YC
authors.lastname: Cheng
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000840:Anisoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D061565:Cycloaddition Reaction; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000438:Alcohols; D000840:Anisoles; D013764:Tetrahydronaphthalenes; C005299:veratrole