Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine

A regio‐ and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium‐catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane add...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2016-04, Vol.55 (15), p.4798-4802
Main Authors: Müller, Jonas M., Stark, Christian B. W.
Format: Article
Language:English
Subjects:
Accessibility
alkaloids
Derivatives
diastereodivergent reactions
Indoles
Iridium
Isomers
Ligands
prenylation
Stereoisomers
Stereoselectivity
total synthesis
Tryptophan
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A regio‐ and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium‐catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane additive and can be switched by changing the nature of the borane. One enantiomer of the ligand is thus sufficient to prepare all possible isomers. The synthetic potential of this method was demonstrated by a short total synthesis of amauromine and its two natural diastereomers. Asymmetric prenylation: A regio‐ and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium‐catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane additive and can be switched by changing the nature of the borane.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201509468