Total synthesis of (±)-paniculide-a

PA Jacobi, CSR Kaczmarek, UE Udodong

Index: Jacobi, Peter A.; Kaczmarek, Colleen S.R.; Udodong, Uko E. Tetrahedron, 1987 , vol. 43, # 23 p. 5475 - 5488

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Citation Number: 37

Abstract

An efficient synthesis of the paniculide A precursor 4 has been achieved beginning with 3- methylglutaric anhydride, and utilizing as the key step an intramolecular Diels-Alder reaction of an acetylenic oxazole to give a 2-methoxyfuran. Acid hydrolysis then provided the requisite butenolide ring characteristic of the paniculides.