Luciduline: a unique type of Lycopodium alkaloid

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Abstract
The isolation and determination of the structure of luciduline, C13H21ON, an alkaloid present among the weak bases of Lycopodium lucidulum Michx, is described. Chemical and physical evidence which suggests structure 9 for luciduline is presented. An X-ray diffraction study on O-p -bromobenzoyl-dihydroluciduline confirmed this hypothesis and defined the stereochemistry of the methyl group at C-8. The complete structure of luciduline, including absolute configuration, is thus represented by 1. A possible mode of biosynthesis of luciduline, which is a new type of Lycopodium alkaloid, is discussed. The mass spectra of luciduline and some of its derivatives are interpreted in terms of structure 1.

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