Catalytic Asymmetric Polycyclization of Tertiary Enamides with Silyl Enol Ethers: Total Synthesis of (-)-Cephalocyclidin A.
J Am Chem Soc
; 145(49): 26550-26556, 2023 Dec 13.
Article
in En
| MEDLINE
| ID: mdl-38019148
ABSTRACT
A catalytic enantioselective polycyclization of tertiary enamides with terminal silyl enol ethers has been developed by virtue of Cu(OTf)2 catalysis with a novel spiropyrroline-derived oxazole (SPDO) ligand. This tandem reaction offers an effective approach to assemble bicyclic and tricyclic N-heterocycles bearing both aza- and oxa-quaternary stereogenic centers, which are primal subunits in a range of natural alkaloids. Strategic application of this methodology and a late-stage radical cyclization as key steps have been showcased in the concise total synthesis of (-)-cephalocyclidin A.
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01-internacional
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MEDLINE
Language:
En
Journal:
J Am Chem Soc
Year:
2023
Document type:
Article
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