Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7435-7470Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301061r
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Funding
- National Institutes of Health [P50 GM086145, P41 GM089169]
- Chicago Biomedical Consortium
- Searle Funds at the Chicago Community Trust
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We describe a unified synthetic strategy for efficient assembly of four new heterocyclic libraries. The synthesis began by creating a range of structurally diverse pyrrolidinones or piperidinones. Such compounds were obtained in a simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by providing rapid entry into a wide range of bicyclic and tricyclic dienamides. The final stage of the process entailed diversification of each of the initially produced carboxylic acids using a fully automated platform for amide synthesis, which delivered 1872 compounds in high diastereomeric and chemical purity.
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