Leporin A: an antiinsectan N-alkoxypyridone from the sclerotia of Aspergillus leporis

Tetrahedron Letters
1991.0

Abstract

Leporin A (5), an antiinsectan N-methoxy-2-pyridone, was isolated from the sclerotia of Aspergillus leporis. The structure was determined through analysis of various 1D- and 2D-NMR experiments. Two previously reported aflavinine derivatives (3 and 4) were also isolated from this source. Sclerotia are important physiological structures produced by certain fungi that serve as a principal mechanism for species survival and propagation. Fungivorous insects often encounter dormant sclerotia in soil, and may represent a threat to their survival. We have reported the isolation of a series of antiinsectan indole diterpenoids (e.g. dihydroxyaflavinine; 1 and nominine; 2) from the sclerotia of several Aspergillus spp. We now wish to report the isolation and structure of leporin A, a structurally unrelated antiinsectan metabolite from the sclerotia of Aspergillus leporis (NRRL 3216). Leporin A contains an unusual N-methoxypyridone moiety, as well as a ring system not previously encountered from a natural source.

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