Atheroline from

The determination of the position of the phenolic group in moschatoline is based mostly on UV data. Both moschatoline and the related alkaloid atheroline (7), obtained from the same source, show strong bathochromic shifts upon addition of base. The synthetic 1-hydroxy-... 

D ring substituents may also cleave with the aid of the C-7 keto group. The concerted loss of CH3OH (or CHgOD) from atheroline (7) is diagrammed in Scheme 8. 

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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