Lycopodium Alkaloids: Isolation and Asymmetric Synthesis

Abstract

Lycopodium alkaloids have attracted the attention of many natural product chemists and synthetic organic chemists due to their important biological activities and unique skeletal characteristics. In this review we describe isolation and asymmetric syntheses of several new alkaloids such as lycoposerramines-C, -V, -W, and cernuine, and show that asymmetric total synthesis played a key role in elucidating the structures of these complex natural products.

Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II)

“…Supplementary dataSupporting Information File 1 (NMR spectra of compound 12) Chemical structure of isolated compounds(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15).…”

Dendritic cells matured in the presence of the lycopodium alkaloid annotine direct T cell responses toward a Th2/Treg phenotype

“…All rights reserved. have been described so far (Kitajima and Takayama 2012;Ma and Gang 2004;Olafsdottir et al 2013). Most of these compounds have been isolated in a very limited amount, just enough for structure elucidation.…”

Lycopodium alkaloids from Palhinhaea cernua

“…2 The chemical constituents of the genus Lycopodium (sensu lato) plants are mainly Lycopodium alkaloids which are quinolizine or pyridine and α-pyridone type alkaloids. [3][4][5][6][7][8][9][10] Some of these alkaloids inhibit acetylcholinesterase (AChE) and provide a challenge for total synthesis. [9][10] In our previous research on this plant, palhinine A, a novel C 16 N-type alkaloid was isolated.…”

“…[3][4][5][6][7][8][9][10] Some of these alkaloids inhibit acetylcholinesterase (AChE) and provide a challenge for total synthesis. [9][10] In our previous research on this plant, palhinine A, a novel C 16 N-type alkaloid was isolated. 9 We now report the isolation and structural elucidation of two new Lycopodium alkaloids (1-2) along with ten previously identified compounds (Figure 1), namely, lycoflexine N-oxide (3) 8 , lycoflexine (4), 11 lycodine (5), 12 α-obscurine (6), 12 dehydroisofawcettiine (7), 13,14 lycopodine (8), 14 5-acetyllycofoline (9), 15 acetylfawcettiine (10), 16,17 cernuine (11) 18 and lycocernuine (12).…”