Regiodivergent Addition of Phenols to Allylic Oxides: Control of 1,2- and 1,4-Additions for Cyclitol Synthesis†
Matthew J. Moschitto
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDavid N. Vaccarello
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Chad A. Lewis
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)Search for more papers by this authorMatthew J. Moschitto
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDavid N. Vaccarello
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Chad A. Lewis
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)
Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA)Search for more papers by this authorThe project described was supported by Award Number T32GM008500 (M.J.M.) from the National Institute of General Medical Sciences and generously supported by Cornell University. We thank Anthony Condo for mass spectra data collection and Ivan Keresztes for assistance with the NMR spectra.
Abstract
Control of 1,2- and 1,4-addition of substituted phenols to allylic oxides is achieved by intercepting palladium π-allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK 7607, cyathiformine B type, streptol, and a new cyclitol.
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References
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