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Updated: Jul 24, 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 scalable route to trisubstituted (E)-vinyl bromides.
Cheon-Gyu Cho1, Won-Suk Kim, Amos B Smith
1Department of Chemistry, Hanyang University, Seoul, Korea 133-791. ccho@hanyang.ac.kr
A new two-step synthesis efficiently creates trisubstituted (E)-vinyl bromides from unsaturated lactones. This scalable method yields key intermediates for complex natural products like tedanolide.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Trisubstituted (E)-vinyl bromides are valuable synthetic intermediates.
- Existing methods for their synthesis can be limited in scope or scalability.
Purpose of the Study:
- To develop an effective and scalable two-step synthesis for trisubstituted (E)-vinyl bromides.
- To demonstrate the utility of this protocol for preparing complex molecules.
Main Methods:
- The synthesis involves bromination of alpha,beta-unsaturated lactones.
- A subsequent hydrolytic fragmentation step yields the desired vinyl bromides.
Main Results:
- The protocol is effective and readily scalable.
- Multigram quantities of key intermediates, such as (+)-(E)-4-bromo-2-methyl-3-pentenol, were synthesized.
- This intermediate is crucial for the synthesis of natural products (+)-tedanolide and (+)-13-deoxytedanolide.
Conclusions:
- A robust and scalable method for synthesizing trisubstituted (E)-vinyl bromides has been established.
- This protocol offers a practical route to important synthetic intermediates for natural product synthesis.
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