Abstract
A novel free radical cyclisation approach for the synthesis of lysergic acid analogues has been investigated. The homolytic cleavage of carbon-bromine bond, mediated by tri-n-butyltin hydride, led to the development of a method for the construction of 3,4-disubstituted dihydroindoles via single cyclisation; hexahydrobenz[cd]indoles via double tandem cyclisations and both octahydroindolo[6,5,4-cd]indoles and decahydroindolo[4,3-fg]quinolines via triple radical cyclisations. A successful tandem double 5-exo-trig,6-endo-trig cyclisation of aryl radical generated from N-3-[3-(N-acetyl-N-allylamino)-2-bromophenyl]-5-(carbomethoxy)-1,4,5,6-tetrahydro-N-methylpyridine afforded methyl 1-acetyl-2,3,9,10-tetrahydrolysergate.
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