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Synfacts 2023; 19(10): 0987
DOI: 10.1055/s-0042-1752206
DOI: 10.1055/s-0042-1752206
Metals in Synthesis
Silver(I)-Catalyzed Rearrangement of 1,4-Disubstituted Cubanes to 1,3- or 2,6-Disubstituted Cuneanes
Smith E,
Jones KD,
O’Brien L,
Argent SP,
Salome C,
Lefebvre Q,
Valery A,
Böcü M,
Newton GN,
Lam HW.
*
University of Nottingham, UK
Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.
J. Am. Chem. Soc. 2023;
145: 16365-16373
DOI: 10.1021/jacs.3c03207
Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.
J. Am. Chem. Soc. 2023;
145: 16365-16373
DOI: 10.1021/jacs.3c03207
Significance
Lam and co-workers disclosed a silver(I)-catalyzed rearrangement of 1,4-disubstituted cubanes to 1,3- or 2,6-disubstituted cuneanes. The regioselectivity is strongly dependent on the electronic character of the substituents.
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Comment
To explore those strained hydrocarbons as isosteres of 1,3-disubstituted benzenes, an analogue of the anticancer drug sonidegib was prepared by replacing the 1,2,3-trisubstituted benzene with a 1,3-disubstituted cuneane.
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Publication History
Article published online:
14 September 2023
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