title: Synthesis of (-)-morphine.
abstract: The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
authors.forename: Douglass F
authors.initials: DF
authors.lastname: Taber
authors.forename: Timothy D
authors.initials: TD
authors.lastname: Neubert
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D009020:Morphine / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000701:Analgesics, Opioid; D009020:Morphine