Cularine N-oxide alkaloids from Ceratocapnos heterocarpa

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

“…More recently, two new alkaloids, (+)-cis-cularine N-oxide (46) and (+)-cis-sarcocapnine N-oxide (47) were isolated from Ceratocapnos heterocarpa (Suau 1996), and (+)-sarcocapnidine N-oxide (48) was isolated from Sarcocapnos baetica subsp, integrifolia . Cycleanine N-oxide (51) was isolated from the stems of Synclisia scabrida, along with the known bisbenzylisoquinoline alkaloids cycleanine, norcycleanine, cocsuline, and cocsoline (Ohiri et al 1983).…”

β-Phenylethylamines and the isoquinoline alkaloids

“…Cularine cis-N-oxide 51a and sarcocapnine cis-N-oxide 51b have been isolated from Ceratocapnos heterocarpa, the relative stereochemistry being deduced from studies of the spectra of cularine cis-and trans-N-oxides prepared from the free base. 76 Clavizepine 5b has been synthesised from the thioketal 52, prepared by an internal Ullmann reaction. An elimination reaction converted this into 53a, which was desulfurised to 53b, and oxidation of this with osmium tetroxide afforded the diol 54.…”

Synthesis of Natural Products on Solid Phases via Copper‐Mediated Coupling: Synthesis of the Aristogin Family, Spiraformin A, and Hernandial

“…Acyclic diaryl ethers are found as structural motifs in bisbenzylisoquinoline alkaloids, [8][9][10][11] in perrottetines, [12][13][14] quinoline alkaloids, [15] tetrahydroisoquinolines, [16] aporphines, [17][18][19][20] dibenzopyrans, [21] neolignans, [22] and biphenyl ethers. [23][24][25][26] Cyclic diaryl ethers can be found as a component of bis(benzoquinolines), [27,28] benzylisoquinoline alkaloids, [29,27] bis(bibenzyls), [30,31] cularines, [32] bastadines, [33,34] several peptidic diaryl ethers [35][36][37][38] and macrocyclic heptanoids, [39,40] as well as acerogenins [41,42] and curcumins ( Figure 1). [43] Various methods were established for the formation of diaryl ethers in solution phase.…”