Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids

The Journal of Organic Chemistry
2019.0

Abstract

Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet-Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1′-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this approach. This study features the role of phosphate in the aqueous-based PSR and provides an atom-efficient, sustainable route to new THIQs. © 2019 American Chemical Society.

Knowledge Graph

Similar Paper

Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
The Journal of Organic Chemistry 2019.0
A Catalytic Asymmetric Pictet–Spengler Platform as a Biomimetic Diversification Strategy toward Naturally Occurring Alkaloids
Journal of the American Chemical Society 2022.0
Synthesis of Hydroxyethyl Derivatives of 1-Aryltetrahydroisoquinoline Alkaloids
Chemistry of Natural Compounds 2014.0
Engineering a norcoclaurine synthase for one-step synthesis of (S)-1-aryl-tetrahydroisoquinolines
Bioresources and Bioprocessing 2023.0
Pentafluorophenol (C<sub>6</sub>F<sub>5</sub>OH) Catalyzed Pictet‐Spengler Reaction: A Facile and Metal‐Free Approach Towards Tetrahydro‐β‐Carbolines
Chemistry – A European Journal 2023.0
Synthesis of Tetrahydroisoquinoline-Alkaloid Analogs with a Diphenyloxide Fragment
Chemistry of Natural Compounds 2022.0
The stereospecific and enantiospecific synthesis of indole alkaloids which culminated in the ambidextrous Pictet–Spengler reaction for the C-19 methyl–substituted sarpagine family
Progress in Heterocyclic Chemistry 2021.0
Interfacing Whole Cell Biocatalysis with a Biocompatible Pictet‐Spengler Reaction for One‐Pot Syntheses of Tetrahydroisoquinolines and Tryptolines**
ChemBioChem 2023.0
Ruthenium Catalyzed Tandem Pictet–Spengler Reaction
Organic Letters 2020.0
One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction
Molecules 2024.0