Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 3954-3958Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01089
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Funding
- JSPS KAKENHI [16H05073]
- MEXT KAKENHI [JP16H01147, JP18H04406]
- AMED Platform for Supporting Drug Discovery and Life Science Research
- Uehara Memorial Foundation
- Hoansha Foundation
- Grants-in-Aid for Scientific Research [16H05073] Funding Source: KAKEN
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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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