Journal
ORGANIC LETTERS
Volume 17, Issue 12, Pages 3070-3073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01350
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Funding
- University of Maryland Computer-Aided Drug Design Center
- Leukemia Research Foundation
- Samuel Waxman Cancer Research Foundation
- NIDA [Y1-DA1101]
- Naval Research Laboratory (NRL)
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A facile synthesis of spirocyclic lactams starting from beta-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.
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