Selective Alkylation: A Biomimetic Reaction of the Antileukemic Triptolides?

Science  30 Aug 1974:
Vol. 185, Issue 4153, pp. 791-793
DOI: 10.1126/science.185.4153.791


The potent antileukemic plant principles triptolide and tripdiolide contain a characteristic hydrogen-bonded 9,11-epoxy-14β-hydroxy system. They alkylate propanethiol in a process which involves opening of the epoxide function with neighboring hydroxyl assistance. The reaction may mimic the inhibition of tumor growth via selective alkylation of the thiol groups of key enzymes concerned with groth regulation.