Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 9247-9268Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01835
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Funding
- Natural Science and Engineering Research Council (NSERC) of Canada
- Canadian Fund for Innovation (CFI)
- Universite de Sherbrooke
- NSERC
- Fonds de Recherche du Quebec en Nature et Technologies (FRQNT)
- Center in Green Chemistry and Catalysis (CGCC)
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An application of a one-pot sequential Vilsmeier-Haack cyclization and intramolecular azomethine ylide 1,3-dipolar cycloaddition toward the total synthesis: of (+/-)-caldaphnidine C is presented. It allowed an efficient formation of three cycles with perfect control of four of the five newly created stereogenic centers including one, all-carbon quaternary center. Two synthetic strategies to produce the key-step precursor, the investigation and optimization of the cyclization partners (nucleophile, azomethine ylide, and dipolarophile), and further derivatization of the cycloadduct are reported.
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