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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
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Efficient microwave assisted access to chiral O-(alpha-protected-aminoacyl)steroids
Alan R Katritzky1, Parul Angrish
1Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, 32611-7200, USA. katritzky@chem.ufl.edu
Steroids
|June 20, 2006
Summary
Microwave irradiation efficiently synthesizes chiral protected aminoacyl and dipeptidoyl steroids, retaining complete chirality. This method uses readily available benzotriazole derivatives and steroidal alcohols.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Steroid Chemistry
Background:
- Steroidal compounds are crucial in medicinal chemistry.
- Developing efficient synthetic routes for functionalized steroids is important.
- Chiral integrity is vital for biological activity of steroid derivatives.
Purpose of the Study:
- To develop a convenient and efficient method for synthesizing chiral O-(alpha-protected-aminoacyl)steroids and O-(alpha-protected-dipeptidoyl)steroids.
- To ensure complete retention of chirality during the synthesis.
- To utilize readily available starting materials.
Main Methods:
- Microwave irradiation was employed as the energy source for the reactions.
- N-(Z-alpha-aminoacyl)benzotriazoles and Z-dipeptidoylbenzotriazole were used as acylating agents.
- Naturally occurring steroidal alcohols served as the steroid backbone.
Main Results:
- Chiral O-(alpha-protected-aminoacyl)steroids (4a-f, 6a-b, 8, 4a+4d) and O-(alpha-protected-dipeptidoyl)steroids (12a,b) were successfully synthesized.
- Isolated yields ranged from 65-96%.
- Complete retention of chirality was observed in all synthesized compounds.
Conclusions:
- Microwave-assisted synthesis provides a rapid and efficient route to chiral protected aminoacyl and dipeptidoyl steroids.
- The method is versatile, allowing for the preparation of various steroid conjugates.
- Complete chirality retention ensures the potential biological utility of the synthesized compounds.
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