70043-74-2Relevant academic research and scientific papers
Condensed Cyclic and Bridged-ring systems. Part 13. Synthesis of the Insect Attractant Hydrocarbon, 9a-Carbamorphinan, and X-Ray Structural Analyses of 9a-Carbamorphinan-10-one and 9a-Carba-14α-morphinan-10-one
Chakraborti, Asit K.,Alam, Shaikh Khairul,Chakraborti, Prabir C.,Dasgupta, Rupak,Chakravarty, Jyotirmoy,et al.
, p. 1243 - 1248 (2007/10/02)
The insect attractant bridged hydrocarbon, (+/-)-9a-carbamorphinan (1) and its inactive epimer, (+/-)-9a-carba-14α-morphinan (2), have been synthesized through (+/-)-9a-carbamorphinan-10-one (3), and (+/-)-9a-carba-14α-morphinan-10-one (4), prepared by polyphosphoric acid-catalysed cyclization of the double-bond isomeric benzyloctalins (7), derived from Huang-Minlon reduction of 1-benzyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one (6), followed by the benzylic oxidation with chromic acid.The reduction of the easily accessible (+/-)-9a-carbamorphinan-16-one (10), the orthophosphoric acid-induced cyclization product of (6), provides an efficient alternative route to (1).The structures of the epimeric ketones (3) and (4) have been established by X-ray analysis.
