Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B
Publication type: Journal Article
Publication date: 2017-05-04
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
28471011
General Chemistry
Catalysis
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).
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19
Total citations:
19
Citations from 2024:
2
(10%)
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GOST
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Odagi M. et al. Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 23. pp. 6609-6612.
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Odagi M., Furukori K., Takayama K., NOGUCHI K., Nagasawa K. Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 23. pp. 6609-6612.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201701431
UR - https://doi.org/10.1002/anie.201701431
TI - Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B
T2 - Angewandte Chemie - International Edition
AU - Odagi, Minami
AU - Furukori, Kota
AU - Takayama, Kan
AU - NOGUCHI, Keiichi
AU - Nagasawa, K.
PY - 2017
DA - 2017/05/04
PB - Wiley
SP - 6609-6612
IS - 23
VL - 56
PMID - 28471011
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Odagi,
author = {Minami Odagi and Kota Furukori and Kan Takayama and Keiichi NOGUCHI and K. Nagasawa},
title = {Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B},
journal = {Angewandte Chemie - International Edition},
year = {2017},
volume = {56},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/anie.201701431},
number = {23},
pages = {6609--6612},
doi = {10.1002/anie.201701431}
}
Cite this
MLA
Copy
Odagi, Minami, et al. “Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B.” Angewandte Chemie - International Edition, vol. 56, no. 23, May. 2017, pp. 6609-6612. https://doi.org/10.1002/anie.201701431.