Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B |
| |
Authors: | Dr Minami Odagi Kota Furukori Kan Takayama Prof Dr Keiichi Noguchi Prof Dr Kazuo Nagasawa |
| |
Institution: | 1. Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Tokyo, 184-8588 Japan;2. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588 Japan |
| |
Abstract: | 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). |
| |
Keywords: | Kinetische Racematspaltung Naturstoffe Organokatalyse Strukturaufklärung Totalsynthesen |
|
|