Total Synthesis of (+/-)-Leporin A

Barry B. Snider; Qing Lu

doi:10.1021/jo952053i

Total Synthesis of (+/-)-Leporin A

J Org Chem. 1996 Apr 19;61(8):2839-2844. doi: 10.1021/jo952053i.

Authors

Barry B. Snider¹, Qing Lu

Affiliation

¹ Department of Chemistry, Brandeis University, P.O. Box 9110, Waltham, Massachusetts 02254.

PMID: 11667120
DOI: 10.1021/jo952053i

Abstract

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).