Journal
ORGANIC LETTERS
Volume 19, Issue 14, Pages 3739-3742Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01566
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Funding
- Natural Science and Engineering Research Council (NSERC) of Canada
- Universite de Sherbrooke
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A suitably functionalized tricyclic adduct,Containing the Ne common A,B,E rings found in calyciphylline B-type alkaloids was obtained in nine linear steps. The key transformation features an efficient one-pot sequence of intramolecular Vilsmeier-Haack cyclization and azomethine ylide 1,3-dipolar cycloaddition in which three cycles, three new carbon-carbon bonds, and three stereocenters are formed, one being fully substituted. This work also demonstrates the first use of a chiral, nonracemic cyclic enol ether as an internal carbon nucleophile.
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