Synthesis of (-)-morphine.
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.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Neubert
Timothy D
TD
Rheingold
Arnold L
AL
D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D009020:Morphine / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000701:Analgesics, Opioid; D009020:Morphine