Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision
Yuzo Mogi
1
,
Kazato Inanaga
2
,
M. Ihara
2
,
Yousuke Yamaoka
1
,
Kenichi Yamada
1
,
Kiyosei Takasu
1
Publication type: Journal Article
Publication date: 2019-05-22
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31117698
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A multicomponent domino reaction involving three mechanistically distinct Tf2NH-catalyzed reactions was developed. The reaction cascade enables the assembly of a skewed 5/6/4 tricyclic motif with migration of the reactive site with the assistance of a catalyst. The tricyclic product was used to achieve the first total synthesis of cytotoxic paesslerin A by regioselective C-H insertion of the sulfonyl carbenoid and base-promoted olefin isomerization. Our results led to the revision of the originally proposed tricyclic structure of paesslerin A.
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22
Total citations:
22
Citations from 2024:
3
(13.64%)
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GOST
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Mogi Y. et al. Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision // Organic Letters. 2019. Vol. 21. No. 11. pp. 3954-3958.
GOST all authors (up to 50)
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Mogi Y., Inanaga K., Tokuyama H., Ihara M., Yamaoka Y., Yamada K., Takasu K. Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision // Organic Letters. 2019. Vol. 21. No. 11. pp. 3954-3958.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b01089
UR - https://doi.org/10.1021/acs.orglett.9b01089
TI - Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision
T2 - Organic Letters
AU - Mogi, Yuzo
AU - Inanaga, Kazato
AU - Tokuyama, Hidetoshi
AU - Ihara, M.
AU - Yamaoka, Yousuke
AU - Yamada, Kenichi
AU - Takasu, Kiyosei
PY - 2019
DA - 2019/05/22
PB - American Chemical Society (ACS)
SP - 3954-3958
IS - 11
VL - 21
PMID - 31117698
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Mogi,
author = {Yuzo Mogi and Kazato Inanaga and Hidetoshi Tokuyama and M. Ihara and Yousuke Yamaoka and Kenichi Yamada and Kiyosei Takasu},
title = {Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.9b01089},
number = {11},
pages = {3954--3958},
doi = {10.1021/acs.orglett.9b01089}
}
Cite this
MLA
Copy
Mogi, Yuzo, et al. “Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision.” Organic Letters, vol. 21, no. 11, May. 2019, pp. 3954-3958. https://doi.org/10.1021/acs.orglett.9b01089.