10.1021/jo501376q.s002
Emmanuel
B. Castillo-Contreras
Emmanuel
B.
Castillo-Contreras
Alexander
M. Stahl
Alexander
M.
Stahl
Gregory R. Dake
Gregory R.
Dake
Annulated Isoxazoles via [3
+ 2] Cycloaddition of
Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination
American Chemical Society
2014
sequence
elimination
intramolecular
oxime function
hydrogen bromide
cycloaddition
conversion
carbonate
substitution
oximoyl chloride
Annulated Isoxazoles
equivalent
Alkenyl Bromides
tetracyclic isoxazoles
formation
bromo
Promoted
Ag
EliminationSubstituted
Oximoyl Chlorides
salicylaldehyde
Cycloaddition
2014-08-01 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Annulated_Isoxazoles_via_3_2_Cycloaddition_of_Alkenyl_Bromides_and_Oximoyl_Chlorides_and_Ag_I_Promoted_Elimination/2269231
Substituted
salicylaldehydes are converted to fused tetracyclic
isoxazoles through a synthetic sequence incorporating substitution
of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion
to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and
elimination of an equivalent of hydrogen bromide using silverĀ(I) carbonate.
Six examples of this sequence are presented.