The alkaloids of L. magellanicum and the structure of magellanine

Abstract

Examination of the alkaloids of Lycopodium magellanicum (Palisot de Beauvois) has revealed the presence of five alkaloids of established structure and a previously unreported alkaloid, magellanine (C17H25NO2). The ring System of magellanine, deduced from an examination of its spectroscopic properties, is identical with that of paniculatine. The structure of magellanine has been confirmed, and its relative stereochemistry established, in an X-ray crystallographic study.

Synthesis of Cyclohexane-Angularly-Fused Triquinanes

“…Magellanine (68, Scheme 12), a natural product of the Lycopodium alkaloid class, 35 was first isolated from the club moss Lycopodium magellanicum in 1976 and contains a 6-5-5-6 tetracyclic core, including a N-methylpiperidine ring and six stereogenic centers. 36 Eight total syntheses of magellanine have been reported, 37 along with the synthesis of other naturally occurring analogues such as magellaninone (69) 37d-h,38 and paniculatine (70), 37d-f,39,40 the oxidation state of which differ in either the A or B ring, respectively. Three of these approaches have utilized the 6-5-5-5…”

Isolation of a new lycodine alkaloid from Lycopodium japonicum

“…(Nakashima et al 1975), huperzinine (3)(Yin et al 2006), b-obscurine (4)(Castillo et al 1976), a-obscurine (5)(Nakashima et al 1975) and des-N-methyl-a-obscurine (6).…”

Development of New Gold (I)‐Catalyzed Carbocyclizations and their Applications in the Synthesis of Natural Products

“…Having demonstrated the efficiency of the Au(I)‐catalyzed DDA to generate complex carbocycles from simple starting materials, we applied this method to the total synthesis of magellanine ( 1 a ). This natural product was isolated in 1976 from the club moss Lycopodium magellanicum . A cursory inspection of this alkaloid reveals a tetracyclic angular framework containing 6 contiguous stereogenic centers.…”