Amyris of Jamaica. Nicotinamides of D.C., (Rutaceae)

Tetrahedron Letters
1978.0

Abstract

Unlike most rutaceous genera, Amyris has attracted little attention of chemists. Recently, coumarins were reported in A. simplicifolia and A. madrensis, and re-examination of the essential oil of A. balsamifera yielded several sesquiterpenes. We now describe two nicotinamides from the benzene extract of the Jamaican variety of Amyris plumieri, a plant reclassified as Rutaceae from Burseraceae. Compound I (C₁₉H₂₀N₂O₂) was characterized as a C-substituted chromene nicotinamide via UV, IR, ¹H NMR, mass spectral data, hydrogenation to dihydroderivative II, and biogenetic synthesis. Compound III (C₁₆H₁₈N₂O₃) was identified as a trans-styryl nicotinamide based on spectral analysis, hydrogenation to IV, and ozonolysis. The presence of chromene and amide moieties, along with the masked nicotinamide O-dimethylallyl halfordinol (V, an oxazole found only in Rutaceae), supports the rutaceous classification of A. plumieri. Compounds I and III are the first reported unmasked nicotinamides in Rutaceae.

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