Application of the Asymmetric Pictet-Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds.
Tetrahydroisoquinolines are the framework of numerous natural products predominantly alkaloids, an important and one of the most wide spread families of naturally occurring compounds in the plant kingdom. Tetrahydroisoquinolines are commonly constructed through an old reaction, the so-called Pictet−Spengler Reaction (PSR). In this reaction, a β-aryl ethylamine undergoes an acid mediated condensation with a suitable aldehyde or ketone, followed by ring closure. In this review, we aim to highlight the applications of the asymmetric variant of this old name reaction in the total synthesis of natural products, chiefly, alkaloids, which exhibit significant biological properties.
['M Heravi|Majid|M|', 'Zadsirjan|Vahideh|V|', 'Malmir|Masumeh|M|']
D001688:Biological Products D002384:Catalysis D002625:Chemistry, Organic D013237:Stereoisomerism D044005:Tetrahydroisoquinolines
total synthesis natural products biologically active compounds tetrahydroisoquinolines β-aryl ethylamine asymmetric Pictet–Spengler reaction