De novoasymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation.
The first synthesis of any and all members of the mezzettiaside family of natural products has been achieved. The reported synthesis features the iterative use of the Taylor catalyst in a dual nucleophilic boron/electrophilic palladium catalyzed regioselective glycosylation. In addition, thede novoapproach utilizes atomless protecting groups and the minimal use of protecting groups (2 chloroacetates for the synthesis of 10 natural products). These divergent syntheses occurred in a range of 13 to 22 longest linear steps and required only 41 total steps to prepare the entire family of mezzettiasides.
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115.
Sumit O
SO
Bajaj
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115.
Ehesan U
EU
Sharif
Department of Chemistry, West Virginia University, Morgantown, WV 26506.
Novruz G
NG
Akhmedov
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115.
George A
GA
O'Doherty