Lycopodium Alkaloids – Synthetic Highlights and Recent Developments

The Genus Diphasiastrum and Its Lycopodium Alkaloids

“…Along this line, Wagner and Beitel stated: "The Lycopodiaceae as we know them are diverse modern survivors of an ancient lineage" [5]. Club mosses are incredibly effective chemical factories and produce an array of secondary metabolites called lycopodium alkaloids [6][7][8]. It is fascinating to imagine that maybe these ancient plants were producing the same or similar alkaloids already very early in the evolutionary history of terrestrial plants, and that these compounds might have contributed to their survival.…”

“…Club mosses have been used in traditional medicine for centuries and have been valuable herbal medicines in different ethnic societies around the world. The application of club moss spores from, e.g., Lycopodium clavatum L. (Lycopodiaceae) or Diphasiastrum complanatum (L.) Holub directly to wounds and rashes is well known from natives in North America and Europe [8]. In Ice-…”

Synthesis of quinolizidine-containing lycopodium alkaloids and related natural products

“…The reproduction of these club mosses happen via gametes in an underground sexual phase or via the spores in an alternating life cycle. 1 These plants have been used for millennia for treatments of a wide range of ailments in traditional folk medicines -from controlling fever to schizophrenia to memory loss. 2 These club mosses were also widely used in the ancient cultures in several parts of world as essential herbal remedies.…”

Phlefargesiine A, a C16N2 Lycopodium alkaloid with an unprecedented [6/7/6/6]-tetracyclic skeleton from Phlegmariurus fargesii

“…The13 C NMR spectrum (in CD3 OD) of 1, with the aid of DEPT and HSQC NMR experiments, showed sixteen well-resolved signals comprising one lactam carbonyl group (d 165.5), four sp 2 (d 175.9, 143.5, 143.3, 121.6) and one oxygen-bearing sp 3 (d 68.9) quaternary carbons, three sp 2 (d 144.3, 123.4, 117.5) and two sp 3 (d 53.3, 42.9) methines, four sp 3 methylenes (d 48.4, 30.2, 29.5, 18.0), and one methyl group (d 21.…”

“…5 Biosynthetic pathways for the known lycodine-and phlegmarine-type alkaloids have been well-documented. [1][2][3] Herein, the plausible biogenetic pathways of phlefargesiine A (1) featuring an unprecedented [6/7/6/6]-tetracyclic framework are proposed in Scheme 1. Compound 1 could be either generated from a lycodine-type (e.g., huperzine B) precursor via the Wagner-Meerwein rearrangement 20 (1,2-alkyl shift) followed by a series of dehydration and oxidation (path a), or could be directly derived from a phlegmarine-type precursor by forming a new linkage between C-4 and C-14 (path b) to afford the novel [6/7/6/6]-tetracyclic skeleton.…”