Application of Phenolic Oxidation to the Total Syntheses of the Isoquinoline and Related Alkaloids; Biogenetic Type Synthesis

Abstract

Oxidative radical coupling of phenols between the phenolic oxygen atom or a carbon atom ortho or para to the hydroxy group and those of another phenol to form C-C or C-O bonds is called phenolic oxidation. This type of reaction plays an important role in the biogenesis of many natural products. The present article gives a survey of the total synthesis of isoquinoline alkaloids by phenolic oxidation. 1. Simple Isoquinoline Alkaloids 2. 2-Benzylisoquinoline Series 3. 1-Benzylisoquinoline Series 3.1. Cularine and Related Alkaloids 3.2. Bis-benzylisoquinoline Alkaloids 3.3. Aporphine and Proaporphine Alkaloids 3.4. Dibenzopyrrocoline Alkaloids (Indolo[2,1-a]isoquinoline Alkaloids) 3.5. Morphinanedienone Alkaloids 3.6. Erythrina Alkaloids 3.7. Phenanthroquinolizidine Alkaloids 4. Amaryllidaceae Alkaloids 5. Phenethylisoquinoline Alkaloids