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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total synthesis of (-)-isoschizogamine
Yusuke Miura1, Noriyuki Hayashi, Satoshi Yokoshima
1Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|July 12, 2012
Summary
The first asymmetric total synthesis of (-)-isoschizogamine was achieved. Key steps included a Wagner-Meerwein rearrangement and tandem metathesis for efficient carbon framework construction.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- (-)-Isoschizogamine is a complex natural product.
- Efficient synthetic routes are crucial for accessing such molecules.
Purpose of the Study:
- To achieve the first asymmetric total synthesis of (-)-isoschizogamine.
- To develop a facile and efficient synthetic strategy.
Main Methods:
- Wagner-Meerwein rearrangement for carbon framework construction.
- Tandem and ring-closing metathesis reactions.
- Stereoselective rhodium-mediated 1,4-addition of arylboronic acid.
- Hemiaminal ether cyclization.
Main Results:
- Successful construction of the (-)-isoschizogamine carbon skeleton.
- Demonstration of key synthetic transformations including rearrangements and metathesis.
- Establishment of stereochemical control throughout the synthesis.
Conclusions:
- The first asymmetric total synthesis of (-)-isoschizogamine is reported.
- The developed synthetic route is efficient and highlights novel applications of key reactions.
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