A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine

作者：Cannon Jeffrey S^*

来源：Organic Letters, 2018, 20(13): 3883-3887.

DOI：10.1021/acs.orglett.8b01464

An enantioselective route to the C,D-bicycle of massadine is reported. Enantiopure intermediates were generated by a single stereoselective reduction using the Corey-Bakshi-Shibata reagent. This initial stereoinduction was translated into the five contiguous stereocenters of the massadine D-ring by a synthetic route that features a diastereoselective and stereospecific Ireland Claisen rearrangement of a trianionic enolate followed by a diastereoselective nitrone dipolar cycloaddition of a highly electron poor oxime.

• 出版日期2018-7-6