3 years ago

Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B

Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B
Keiichi Noguchi, Kan Takayama, Kazuo Nagasawa, Minami Odagi, Kota Furukori
Described herein is the enantioselective syntheses of (+)- and (−)-rishirilide B from the corresponding optically active β-substituted tetralones, which were obtained by oxidative kinetic resolution based on α-hydroxylation in the presence of a chiral guanidine-bisurea bifunctional organocatalyst. Benzylic oxidation of the tetralones at C1 followed by regioselective isomerization of the oxabenzonorbornadiene structure led to rishirilide B. Our findings lead to the revision of the previously proposed (2R,3R,4R) absolute configuration of (+)-rishirilide B to (2S,3S,4S). Reconfigured: Enantioselective synthesis of (+)- and (−)-rishirilide B has been achieved from optically active β-substituted tetralone, which was obtained by oxidative kinetic resolution using a guanidine-bisurea bifunctional organocatalyst. This synthetic studies led to revision of the previously proposed absolute configuration of (+)-rishirilide B to (2S,3S,4S).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701431

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