Dimethyldioxirane → HCID 16195253, compound

Participants

Reaction Steps

Epoxidation of the C-27, C-28 Double Bond of PbTx-2 To Provide PbTx-6. Dimethyldioxirane was generated in a distillation apparatus, connected to a dry ice condenser, according to the procedure described by Adam17 for a small-scale preparation. The receiving flask was charged with PbTx-2 (2.33 mg) in 5.0 mL of acetone and was cooled in an ice/salt bath. The reaction was monitored by HPLC. When all of the PbTx-2 was consumed, the acetone was evaporated in vacuo, and the residue taken up in 1.0 mL of methanol and purified by HPLC to provide 2.25 mg (95%) of PbTx-6. DCI MS (NH3): 911 (M+1), 928 (M+NH4), 893 (M−H2O). 1H and 13C NMR were identical to that reported by Shimizu.

Provenance & Evidence