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Preparation of DMMTAV and DMDTAV Using DMAV for Environmental Applications: Synthesis, Purification, and Confirmation
Published on: March 9, 2018
Total synthesis of muamvatin
1Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon SK S7N 5C9, Canada. dale.ward@usask.ca
Organic Letters
|December 6, 2012
Summary
Enantioselective synthesis of muamvatin was achieved. The study questions muamvatin
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Muamvatin is a complex natural product.
- Its proposed formation mechanism requires investigation.
Purpose of the Study:
- To achieve the enantioselective total synthesis of muamvatin.
- To investigate the cyclization mechanism of muamvatin formation.
Main Methods:
- Sequential substrate-controlled stereoselective aldol reactions.
- Ring-chain tautomerization of an acyclic derivative.
Main Results:
- Successful enantioselective total synthesis of muamvatin.
- The trioxaadamantane tautomer is thermodynamically stable.
- A significant kinetic barrier to cyclization was observed.
Conclusions:
- The synthesis provides a route to muamvatin.
- The observed kinetic barrier casts doubt on the proposed artifactual formation of muamvatin during isolation.
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