Issue 0, 1986
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Asit K. Chakraborti,   Shaikh Khairul Alam,   Prabir C. Chakraborti,   Rupak Dasgupta,   Jyotirmoy Chakravarty,   Usha Ranjan Ghatak,   Apurba Kabiraj  and  Sundar Gopal Biswas  

Abstract

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.

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Article information

DOI
https://doi.org/10.1039/P19860001243
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 1243-1248

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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

A. K. Chakraborti, S. K. Alam, P. C. Chakraborti, R. Dasgupta, J. Chakravarty, U. R. Ghatak, A. Kabiraj and S. G. Biswas, J. Chem. Soc., Perkin Trans. 1, 1986, 1243 DOI: 10.1039/P19860001243

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