Total Synthesis of (+/-)-Leporin A.
An efficient synthesis of (+/-)-leporin A (1) has been developed using a tandem Knoevenagel condensation-inverse electron demand intramolecular hetero Diels-Alder reaction to construct the key tricyclic intermediate 3 from pyridone 5 and dienal 6 in one pot in 35% yield. Hydroxylation (71%) of 3 and methylation (77%) of the resulting hydroxypyridone 2 completed the first total synthesis of (+/-)-leporin A (1).
Snider
Barry B.
BB
Department of Chemistry, Brandeis University, P.O. Box 9110, Waltham, Massachusetts 02254.
Lu
Qing
Q