Oxidative conversion of δ-sultones to γ-lactones.

Delta-sultones, prepared by C-H insertion, can be oxidatively converted to gamma-lactones by treatment with t-BuOK/t-BuOOH. An intermediate in the synthesis of (-)-eburnamonin was prepared using this approach.

SYNTHETICALLY USEFUL INTERMEDIATES BY DIAZOSULFONE AND SULFONATE C-H INSERTION.

Intramolecular C-H insertion on diazosulfone and diazosulfonate substrates was used to prepare synthetically useful intermediates from easily available starting materials.

PRACTICAL PREPARATION OF RESVERATROL 3-O-β-D-GLUCURONIDE.

A practical synthesis of resveratrol 3-O-β-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large scale preparation of resveratrol is also reported.

Enantioselective synthesis of Bakuchiol using diazosulfonate C-H insertion to install the quaternary center.

Bakuchiol was prepared from commercial (-)-citronellol using the diazosulfonate C-H insertion to control the regioselectivity and install the quaternary center.

Formation of six- vs. five-membered cyclic sulfones by C-H insertion.

Selectivity of six- vs. five- membered ring formation in C-H insertion on alkylsulfonyl diazoacetates is sensitive to the substrate structure and catalyst used.