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Download fileA Novel Sequential Aminodiene Diels−Alder Strategy for the Rapid Construction of Substituted Analogues of Kornfeld's Ketone
journal contribution
posted on 2002-10-25, 00:00 authored by Scott K. Bur, Albert PadwaThrough a novel sequence of aminodiene Diels−Alder reactions, amidofurans 18a−c were converted to tricyclic ketones 21a−c 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.