Synthesis of N-benzoylhomomeroquinene ( is carried out using 7-oxyisoquino-line (, which is made by reacting of aminoacetal with m-hydroxybenzaldehyde with isolation of the intermediate imine (, which then cyclizes in the presence of sulfuric acid to the starting substance—7-oxyisoquinoline ( The resulting 7-oxy-isoquinoline is aminomethoxided with a mixture of formaldehyde and piperidine to make 7-oxy-8-piperidinomethylisoquinoline ( Reducing this with hydrogen using a palladium catalyst removes the piperidine fragment, giving 7-oxy-8-methylisoquinoline

( This is again reduced with hydrogen in order to hydrogenate the pyridine fragment, except this time a palladium oxide catalyst is used. This forms 7-oxy-8-methylte-trahydroisoquinoline ( N-Acylating the resulting compound with acetic anhydride and then hydrogenating it with hydrogen using a platinum catalyst gives a mixture of stereoisomeric N-acetyl-7-oxy-8-methyldecahydroisoquinolines, from which the cw-isomer ( is isolated. It is oxidized using chromium(VI) oxide to N-acetyl-7-keto-8-methyldecahydroisoquinoline ( Reacting this with ethyl nitrite in the presence of sodium ethoxide cleaves up the methylcyclohexanone fragment, giving N-acetyl-10-oxyminodihydrohomomeroquinene (, which is then reduced in the presence of a platinum catalyst to the amine ( This undergoes exhaustive methy-lation using methyl iodide to make a quaternary salt (, which is then cleaved on heating in concentrated alkali, giving racemic homomeroquinene ( Successive esterification and subsequent benzoylation of the product gives the ethyl ester of N-benzoylhomomeroquinene (


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