Related Experiment Video
Updated: May 31, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Enantioselective synthesis of (-)-codeine and (-)-morphine
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
A novel synthetic strategy enables the efficient synthesis of opiate and amaryllidaceae alkaloids. This approach utilizes palladium-catalyzed reactions and visible light photochemistry to construct complex molecular architectures.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Opiate and Amaryllidaceae alkaloids are complex natural products with significant pharmacological properties.
- Existing synthetic routes often involve numerous steps and challenging stereochemical control.
Purpose of the Study:
- To develop a novel, efficient synthetic strategy for opiate and Amaryllidaceae alkaloids.
- To establish stereochemical control early in the synthesis using asymmetric catalysis.
Main Methods:
- Palladium-catalyzed asymmetric allylic alkylation for stereochemical control.
- Heck vinylation for constructing the fourth ring of codeine/morphine.
- Visible light-promoted hydroamination for final ring formation.
Main Results:
- A pivotal tricyclic intermediate was synthesized in six steps.
- (-)-Galanthamine was accessed in two additional steps from the intermediate.
- Codeine and morphine were synthesized, with morphine obtained via high-yield demethylation.
Conclusions:
- The developed strategy provides an efficient route to valuable alkaloid natural products.
- The methodology showcases the utility of modern catalytic methods in complex molecule synthesis.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Regioselective Formation of Enolates
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Opioid Receptors: Overview
Opioid Analgesics: Morphine and Other Natural Cogeners
Opioid Analgesics: Synthetic and Semisynthetic Opioids