Phenethylisoquinolines synthesis

Homopavinane (57) and homoisopavinane (58) ring systems represent examples of the phenethylisoquinoline alkaloid class. A synthesis of racemic... 

Although biosynthesis of the phenethylisoquinoline alkaloids has not yet been studied in full, that of androcymbines, homoaporphines, and homoerythrinans has been examined by work with radioactive tracers. In this section tracer experiments as well as hypothetical biogenetic routes in the synthesis of the phenethylisoquinoline alkaloids are discussed. 

Since the total synthesis of O-methylandrocymbine (17) was accomplished via a photolytic cyclodehydrobromination reaction of a l-(2-bromophenethyl)-7-hydroxyisoquinoline (67), many phenethylisoquinoline alkaloids have been synthesized by this reaction. Irradiation of the bromoisoquinoline 113a,b with a Hanovia 450-W mercury lamp, using a Pyrex filter, in the presence of an excess of sodium hydroxide and sodium hydrogen sulfite gave alkaloid CC-24 (83a) (68) and the homoaporphine 114 (69), respectively. 

Simple Phenethylisoquinolines.—The alkaloid (—)-autumnaline (210) from Colchicum cornigerum (Liliaceae, subfamily Wurmbaeoidae) possesses the absolute configuration shown, and its synthesis has been carried out. ... 

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