Regioselective aryl radical cylization. Part 2.1 Synthesis of octahydro-1H-dibenzo[a,d]cycloheptenes through 7-endo ring closure

Ghosh, Ajit K. ; Mukhopadhyaya, Jayanta K. ; Ghatak, Usha Ranjan (1997) Regioselective aryl radical cylization. Part 2.1 Synthesis of octahydro-1H-dibenzo[a,d]cycloheptenes through 7-endo ring closure Journal of the Chemical Society, Perkin Transactions 1 (18). pp. 2747-2756. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1997...

Related URL: http://dx.doi.org/10.1039/A702253K

Abstract

A simple convergent synthesis of trans- and cis-octahydro-1H-dibenzo[a,d] cycloheptenes 15a-c and 16a-c and 20a-c and 21a-c through implementation of a regioselective 7-endo-trig-aryl radical cyclisation of the respective 2-(o-bromoarylethyl)-1-methylenecyclohexanes 6a-c and 8a-c with tributyltin hydride is described. The scope of the 7-endo aryl radical cyclisation has been further demonstrated by the synthesis of (2SR,4aRS,11aSR)-methyl 1,1-dimethyl-2,3,4,4a,5,10,11,11a-octahydro-1H-dibenzo[a ,d]cycloheptene-2-carboxylate 29.

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