Atheroline, synthesis

A synthesis of homomoschatoline (1,2,3-trimethoxyoxoaporphine) via a Reissert intermediate and Pschorr cyclization has been described/ and a photolytic synthesis of atheroline (l,2,10-trimethoxy-9-hydroxyoxoaporphine) is now available/ The u.v. spectra of oxoaporphines are strongly dependent on the solvent used. ... 

The use of 2-nitrobenzyl halides in the Reissert alkylation, followed eventually by the Pschorr cyclization, has provided an attractive route to various aporphines (31). Thus this procedure had led to the synthesis of apomor-phine, ° apomorphine derivatives, atheroline, imenine, N-methyl-ovigerine, oconovine, 8-hydroxyaporphines, 10-hydroxyaporphines, ... 

A synthesis of atheroline has been achieved starting from the Bischler-Napieralski product 1 which underwent air oxidation to the imino ketone 2. In the presence of alkali and air, 2 was further oxidized to the 1-benzoyliso-quinoline 3. Debenzylation followed by photolysis in the presence of sodium hydroxide in a quartz vessel furnished atheroline (4), and its structural isomer 5 (see Scheme 14.2). ... 

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