The Structure of Verbenalin

Chatterjee, A.; Parks, Lloyd M.

doi:10.1021/ja01174a506

Cited by 10 publications

(1 citation statement)

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“…During the last decades, numerous macroline/sarpagine correlated indole alkaloids were isolated from different species of Alstonia [ 67 , 70 , 71 ]. Interestingly, the macroline/sarpagine alkaloids originated as a result of folktales, demonstrating the medicinal activities of the plants from which these alkaloids were extracted [ 72 , 73 ]. A range of alkaloids from Alstonia angustifolia were demonstrated to contain antiprotozoal property against Plasmodium falciparum or Entamoeba histolytica in vitro [ 74 ], whereas other sarpagine alkaloids were known to include sedative, ganglionic blocking, antibacterial or hypoglycemic properties [ 70 ].…”

Section: Pictet–spengler Reaction In the Total Synthesis Of Naturamentioning

confidence: 99%

Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds

2018

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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.

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