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- Title
Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B.
- Authors
Odagi, Minami; Furukori, Kota; Takayama, Kan; Noguchi, Keiichi; Nagasawa, Kazuo
- 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).
- Subjects
ANTHRACENE; ORGANOCATALYSIS; OXIDATION kinetics; ENANTIOSELECTIVE catalysis; TETRALONES; CHEMICAL synthesis
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 23, p6709
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201701431