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Updated: Jun 18, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
A concise palladium-catalyzed carboamination route to (+/-)-tylophorine
Lana M Rossiter1, Meagan L Slater, Rachel E Giessert
1Medicinal Chemistry Department, Albany Molecular Research, Inc. (AMRI), P.O. Box 15098, 26 Corporate Circle, Albany, New York 12212-5098, USA.
Researchers synthesized the natural product tylophorine using a palladium-catalyzed carboamination method. This efficient approach provides a new route for constructing complex molecules like tylophorine.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Tylophorine is a complex natural product with potential pharmacological properties.
- Efficient synthetic routes are crucial for accessing and studying natural products.
Purpose of the Study:
- To demonstrate the total synthesis of racemic tylophorine.
- To showcase the utility of the palladium-catalyzed Wolfe carboamination method in natural product synthesis.
Main Methods:
- Preparation of an electron-rich aryl bromide intermediate.
- Palladium-catalyzed Wolfe carboamination of the aryl bromide with an olefinic carbamate.
- Elaboration of the resulting pyrrolidine intermediate to racemic tylophorine.
Main Results:
- The synthesis successfully yielded racemic tylophorine.
- The Wolfe carboamination provided the key 2-(arylmethyl)pyrrolidine intermediate in good yield.
- The study validates the carboamination protocol for natural product construction.
Conclusions:
- The palladium-catalyzed Wolfe carboamination is a viable and effective method for synthesizing tylophorine.
- This synthetic strategy highlights the method's broad applicability in complex molecule synthesis.
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