Abstract
This chapter discusses the bond cleavage reactions of protoberberines, oxidation of protoberberines, other reactions of protoberberines, and transformation of protoberberines to related alkaloids. The protoberberine alkaloids play important roles as precursors in the biosynthesis of a variety of related isoquinoline alkaloids, such as protopine, phthalideisoquinoline, and spirobenzylisoquinoline. Chemical transformations of protoberberines to these alkaloids are particularly interesting and exciting from the biogenetic viewpoint. Most alkaloids have oxygenated skeletons and are derived through bond cleavage of protoberberine alkaloids. The C–N bond cleavage is a fundamental and key reaction in skeletal rearrangements of protoberberines. The remaining two cleavages, that is, of the C–C and C–O bonds, are not always essential to transformation. Indenobenzazepines are used as key intermediates for synthesis of rhoeadine, protopine, phthalideisoquinoline, and spirobenzylisoquinoline alkaloids.
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