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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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An unusual intramolecular trans-amidation
Heriberto Rivera1, Sachin Dhar1, James J La Clair1
1Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
Tetrahedron
|June 28, 2016
Summary
Researchers discovered a novel intramolecular trans-amidation reaction during studies of actinorhodin biosynthesis. This finding provides insights into the natural cyclization mechanisms of type II polyketide antibiotics.
Area of Science:
- Natural Product Biosynthesis
- Organic Chemistry
- Biochemistry
Background:
- Polyketide biosynthesis involves complex, timed reactions to create natural products.
- Mimicking these biosynthetic pathways aids in total synthesis and reaction discovery.
Purpose of the Study:
- To report an unusual intramolecular trans-amidation reaction.
- To gain insight into the natural cyclization processes of type II polyketide antibiotics.
Main Methods:
- Preparation of stabilized probes for actinorhodin biosynthesis studies.
- Observation and characterization of an intramolecular trans-amidation reaction.
Main Results:
- Discovery of a rapid intramolecular trans-amidation cyclization event.
- The reaction occurred during the synthesis of probes for actinorhodin biosynthesis.
Conclusions:
- The identified reaction offers a new perspective on natural cyclization in polyketide antibiotic biosynthesis.
- This discovery contributes to understanding the mechanisms of type II polyketide formation.
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