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The structurally related natural products (-)-homaline, (-)-hopromine, (-)-hoprominol, and (-)-hopromalinol have been collectively termed the homalium alkaloids. All four alkaloids possess bis-ζ-azalactam structures, but differ only by the identities of the side chain on each lactam ring. Since their isolation (from the leaves of Homalium pronyense Guillaum found in the forests of New Caledonia), there have been several syntheses of homaline, hopromine, hoprominol, and hopromalinol in both racemic and enantiopure forms. The most highly yielding and versatile strategy for their synthesis employs the conjugate addition of an enantiopure lithium amide reagent to an α,β-unsaturated ester as the key stereodefining step. This methodology has been used in the syntheses of all four members of the homalium alkaloid family and their stereoisomers.

Original publication

DOI

10.1016/bs.alkal.2014.09.001

Type

Journal article

Journal

Alkaloids Chem Biol

Publication Date

2015

Volume

74

Pages

121 - 158

Keywords

Alkaloids, Chemistry Techniques, Synthetic, Heterocyclic Compounds, Magnetic Resonance Spectroscopy, Molecular Structure, New Caledonia, Salicaceae, Stereoisomerism