Synthesis of highly functionalized bicyclo[m.n.1]alkanones via a cationic reaction cascade.
[reaction: see text] The acid-mediated Prins/pinacol and the triple domino reactions Diels-Alder/Prins/pinacol were used to construct highly functionalized bicyclo[m.n.1]alkanones 19-29 and 33a-c possessing various ring sizes from ketals 8-18 and 31a-c in 44-96% yields. This approach proves to be highly efficient and reliable to generate high molecular complexity in a single step.
Lavigne
Roch M A
RM
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Riou
Maxime
M
Girardin
Mélina
M
Morency
Louis
L
Barriault
Louis
L