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Concise enantioselective synthesis of diospongins A and B.

Tetrahedron (2013-09-24)
Eric Stefan, Ansel P Nalin, Richard E Taylor
ZUSAMMENFASSUNG

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.