Total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines involving free radical cyclizations induced by tributyltin(IV) hydride

We describe two total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[1,2-f]isoquinolines based on free radical cyclization. One of them includes the cyclization of N-{2-[2-(2-bromophenyl)-1-methoxyethyl]phenylethyl}acetamides and subsequent transformation of the resulting N-[2-(10-methoxy-9,10-dihydro-1-phenanthryl)ethyl]acetamides. The second is based on the known cyclization of 1-(2-bromobenzyl)isochroman-3-ones to 4,5,6a,7-tetrahydrodibenzo[de,g]chroman-3-ones followed by transformation of the resulting 2-(1-phenanthryl)acetamides.