Bioactive cyclobutane-containing alkaloids

Abstract

The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

Advances in Enantioselective C–H Activation/Mizoroki-Heck Reaction and Suzuki Reaction

“…This method provided a complementary protocol for the syntheses of enantioenriched cyclobutanes containing chiral quaternary stereocenters [64,65].…”

“…In 2014, the same group reported a further research for the arylation of methylene β-C(sp 3 )-H bonds of cyclobutanecarboxylic acid derivatives with arylboron reagents using palladium(II) catalyst with chiral mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) as the ligand (Scheme 12) [63]. This method provided a complementary protocol for the syntheses of enantioenriched cyclobutanes containing chiral quaternary stereocenters [64,65]. With the optimized conditions, different cyclopropanes and organoboronic compounds were investigated and the products were obtained in good yields and good to excellent ee ( Figure 3).…”

Naturally occurring plant isoquinoline N-oxide alkaloids: Their pharmacological and SAR activities

“…They encompass a diverse group of more than 200 structures with restricted occurrence in certain higher plant taxa belonging to species Aristolochia, Argemone, Ceratocapnos, Chelidonium, Corydalis, Cynanchum, Dicentra, Fumaria, Papaver, Pergularia, Platycapnos, Rupicapnos, Sarcocapnos, Sanguinera, and Tylophora (Sato 2013;Nakagawa, et al, 2013;Egydio et al, 2013;Dembitsky 2008;Zdarilova et al 2006;Bentley 2005;Dembitsky 2004Dembitsky , 2005Kartsev 2004). …”

[2+2] Photocycloaddition of Symmetrically Disubstituted Alkenes to 2(5H)‐Furanones: Diastereoselective Entry to 1,2,3,4‐Tetrasubstituted Cyclobutanes

“…The most studied among these natural products is the alkaloid (-)-sceptrin (1), which was isolated from the sea sponge Agelas Sceptrum in 1981 [1] and exhibits potent activity as an antiviral, antimuscarinic, antibacterial, and antihistaminic agent. [2] Recently, other 1,2,3,4-tetrasubstituted cyclobutanes have also been isolated from natural sources, [3] such as incarvilateine (2) from Incarvillea sinensis, [4] and dipiperamide A (3) from Piper nigrum (Figure 1). [5] Despite the potent biological activity shown by sceptrin (1), only three synthetic approaches to this interesting compound have been described.…”