Fluorinated and rearranged gedunin derivatives

When treated with (diethylamino)sulfur trifluoride (DAST), 11α-hydroxygedunin gave 11β-fluorogedunin and 9,11-didehydrogedunin, whereas deacetylgedunin afforded two skeletal rearranged products 6 and 7, in which the Me-30 had shifted from position 8 to position 7. Of those products, 11β-fluorogedunin and 6 were shown to be more cytotoxic than gedunin on P-388 leukemia cells.

Highlights► A fluorinated gedunin derivative was prepared from 11α-hydroxygedunin. ► A skeletal rearrangement reaction occurred when deacetylgedunin was treated with DAST. ► The structure of the rearranged product was established by X-ray crystallography. ► Some analogs were found to be more cytotoxic than gedunin.