An Improved Pictet-Spengler Condensation: A Convenient Synthetic Route to Bioactive Manzamine Derivatives

HETEROCYCLES
2007.0

Abstract

An improved Pictet-Spengler method for the construction of a modified β-carboline moiety from an α,β-unsaturated aldehyde is described. The Pictet-Spengler reactions between ircinal A (1) and tryptamine derivatives under milder conditions have resulted in shorter reaction times and higher product yields (70 to 89%) with control of stereochemistry. The Pictet-Spengler products (9 and 11) are two new manzamine alkaloids, which display strong activities against Mycobacterium intracellulare with IC50 values of 0.2 and 0.06 μg/mL, respectively. © 2007 The Japan Institute of Heterocyclic Chemistry.

Knowledge Graph

Similar Paper

An Improved Pictet-Spengler Condensation: A Convenient Synthetic Route to Bioactive Manzamine Derivatives
HETEROCYCLES 2007.0
Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions
Organic & Biomolecular Chemistry 2020.0
Pictet–Spengler Synthesis of Perfluoroalkylated Tetrahydro-γ-carbolines and Tetrahydropyrrolopyrazines
Synthesis 2020.0
Tscheschamine — A New Cyclopeptide Alkaloid from the Bark of Zizyphus sativa Gaertn
HETEROCYCLES 1988.0
Ircinals A and B from the Okinawan marine sponge Ircinia sp.: plausible biogenetic precursors of manzamine alkaloids
The Journal of Organic Chemistry 1992.0
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
Ruthenium Catalyzed Tandem Pictet–Spengler Reaction
Organic Letters 2020.0
Total Synthesis of 6-Hydroxymetatacarboline-<scp>d</scp> Discovered from Mycena metata via the Pictet–Spengler Reaction Followed by the Horner–Wadsworth–Emmons Reaction
ACS Omega 2021.0
Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A
Angewandte Chemie International Edition 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