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An efficient method for synthesis of succinate-based MMP inhibitors
Mukund P Sibi1, Hikaru Hasegawa
1Department of Chemistry and Center for Protease Research, North Dakota State University, Fargo, ND 58105, USA.
Organic Letters
|September 27, 2002
Summary
This study presents a new method for synthesizing disubstituted succinates using radical addition and allylstannane trapping. The synthesized succinates were successfully converted into a matrix metalloproteinase (MMP) inhibitor.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Developing efficient synthetic routes for complex organic molecules is crucial in medicinal chemistry.
- Matrix metalloproteinases (MMPs) are implicated in various diseases, driving the need for novel inhibitors.
Purpose of the Study:
- To develop a novel synthetic strategy for disubstituted succinates.
- To demonstrate the utility of this method by synthesizing a known MMP inhibitor.
Main Methods:
- Employing a radical addition reaction to a differentially protected fumarate.
- Utilizing allylstannane trapping to introduce substituents.
- Subsequent conversion of the succinate product to a target MMP inhibitor.
Main Results:
- Achieved good yields of disubstituted succinates.
- Demonstrated high anti diastereoselectivity in the succinate formation.
- Successfully synthesized a known matrix metalloproteinase inhibitor from the succinate intermediate.
Conclusions:
- The developed radical addition/allylstannane trapping sequence is an effective method for synthesizing disubstituted succinates.
- This methodology provides a viable route towards the synthesis of MMP inhibitors.