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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Improved total synthesis of incednam
Akira Takada1, Kanjiro Uda, Takashi Ohtani
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
The Journal of Antibiotics
|February 7, 2013
Summary
An improved total synthesis of incednam, the aglycon of incednine antibiotic, was achieved. This synthesis utilized intramolecular ring-closing olefin metathesis for macrocycle construction.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Incednine is a 24-membered macrolactam glycoside antibiotic.
- Incednam is the aglycon of incednine.
- Efficient synthesis of complex natural products is crucial for drug discovery.
Purpose of the Study:
- To develop an alternative and improved total synthesis of incednam.
- To establish a robust method for constructing the 24-membered macrolactam core.
Main Methods:
- Total synthesis of incednam.
- Intramolecular ring-closing olefin metathesis (RCM) for macrocyclization.
- Multi-step organic synthesis strategies.
Main Results:
- Successful and improved total synthesis of incednam was accomplished.
- The 24-membered macrocycle was efficiently constructed using RCM as the key step.
- This synthetic route offers an alternative to previously reported methods.
Conclusions:
- The developed synthetic strategy provides a viable and improved route to incednam.
- Intramolecular RCM is a powerful tool for the synthesis of large macrolactams.
- This work contributes to the accessibility of incednine analogs for further biological evaluation.
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