American Chemical Society
ol0268992_si_001.pdf (12.69 kB)

A Novel Sequential Aminodiene Diels−Alder Strategy for the Rapid Construction of Substituted Analogues of Kornfeld's Ketone

Download (12.69 kB)
journal contribution
posted on 2002-10-25, 00:00 authored by Scott K. Bur, Albert Padwa
Through a novel sequence of aminodiene Diels−Alder reactions, amidofurans 18ac were converted to tricyclic ketones 21ac in moderate to good yields. Ketone 21a could be converted to Uhlé's ketone (6) by cleaving the tert-butyl carbamate and oxidatively removing the methyl ester. Tricycle 21a readily underwent bromination to give 22. Formation of the corresponding enol triflate 25 followed by carbonylation gave ester 27, which was then coupled with N-methyl propriolamide to furnish 26.