Dibenzotetracyclic Derivatives. II. Synthesis of 9-Aminoalkyl-9,10-dihydro-9,10-methanoanthracenes

A synthesis of 9-aminoalkyl-9, 10-dihydro-9, 10-methanoanthracenes (2) is reported. A key intermediate, 9-formyl-9, 10-dihydro-9, 10-methanoanthracene (4), was synthesized from 9-amino-12-hydroxy-9, 10-dihydro-9, 10-ethanoanthracene (3b) by nitrous acid deamination. The amino-alcohol (3b) was synthesized in 5 steps starting from anthracene-9-carbaldehyde.