Syntheses of 6-amino-1,2-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol derivatives.

Publisher Website
Google Scholar
Abstract
Investigations on the essential conformation of adrenergic catecholamines led to synthesis of 6-amino-1,2-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol derivatives (1), which are 7-membered rigid analogs of catecholamines. Although catalytic reduction of the amino ketones leading to the analogs of noradrenaline [norepinephrine] and isoproterenol yielded mixtures of 5,6-cis and trans isomers, it was found that lithium aluminum hydride reduction of .alpha.-hydroxyimino ketone gave exclusively cis-amino alcohol (13a-cis) and that reduction of .alpha.-acetamido ketone with sodium borohydride followed by hydrolysis afforded 13a-trans. Several pairs of 5,6-cis and trans isomers of 1 were prepared by catalytic reduction of 13a-cis and 13a-trans or their N-substituted derivatives. N-tert-Butyl derivative was prepared via 13d-trans which was obtained by hydrolysis of an azirizino compound.

This publication has 0 references indexed in Scilit: