Concise enantioselective synthesis of diospongins A and B.
Ether transfer methodology is capable of stereoselectively generating 1,3-diol mono- and diethers in good yield. Surprisingly, allylic and benzylic substrates provide none of the desired products when exposed to previously optimized conditions of iodine monochloride. Herein, second-generation activation conditions for ether transfer have been developed that circumvents undesired side reactions for these substrates. The application of this chemistry to the enantioselective synthesis of diospongins A and B has now been accomplished.
Department of Chemistry and Biochemistry and the Mike and Josie Harper Cancer Research Institute, University of Notre Dame, 251 Niewland Science Hall, Notre Dame, IN 46556, United States.
Eric
E
Stefan
Ansel P
AP
Nalin
Richard E
RE
Taylor
Antiosteoporotic activity; Diospongin; Ether transfer; Radical cyclization