Topic
Mesembrine
About: Mesembrine is a research topic. Over the lifetime, 177 publications have been published within this topic receiving 3078 citations. The topic is also known as: mesembrine.
Papers published on a yearly basis
Papers
Book•
10 Dec 1981
TL;DR: In this paper, the authors present a method for the synthesis of polyacetylenes and prostaglandins from the shikimic acid pathway, which can be classified into three categories: primary, secondary and tertiary.
Abstract: 1 Introduction.- 1.1 Primary and secondary metabolism.- 1.1.1 Introduction.- 1.1.2 Fatty acid biosynthesis.- 1.1.3 The biosynthesis of polyacetylenes and prostaglandins.- 1.2 Stereochemistry and biosynthesis.- 1.2.1 Chirality and prochirality.- 1.2.2 Chiral methyl groups.- 1.2.3 Hydroxylation at saturated carbon atoms.- 1.3 Some reactions of general importance in secondary metabolism.- 1.3.1 Oxidative coupling of phenols.- 1.3.2 Hydroxylation of aromatic substrates.- 1.3.3 Methylation.- References.- 2 Techniques for biosynthesis.- 2.1 Introduction.- 2.2 Isotopic labelling.- 2.2.1 Radioactive isotopes.- 2.2.2 Stable isotopes.- 2.3 Enzymes and mutants.- References.- 3 Polyketides.- 3.1 Introduction.- 3.2 Formation of poly-?-keto-acyl-CoA's.- 3.2.1 Acetate and malonate.- 3.2.2 Assembly of poly-?-keto-acyl-CoA's.- 3.3 Tetraketides.- 3.4 Pentaketides.- 3.5 Hexaketides.- 3.6 Heptaketides.- 3.7 Octaketides.- 3.8 Nona-and deca-ketides.- 3.9 Polyketides with mixed origins and large ring polyketides.- References.- 4 Terpenes and steroids.- 4.1 Introduction.- 4.2 Steroids.- 4.3 Pentacyclic triterpenes.- 4.4 Squalene.- 4.5 Monoterpenes.- 4.6 Sesquiterpenes.- 4.7 Diterpenes.- 4.8 Sesterpenes.- 4.9 Carotenoids and vitamin A.- References.- 5 The shikimic acid pathway.- 5.1 Introduction.- 5.2 Quinones.- 5.3 Coumarins.- 5.4 Flavonoids.- References.- 6 Alkaloids.- 6.1 Introduction.- 6.2 Piperidine and pyrrolidine alkaloids.- 6.2.1 Piperidine alkaloids.- 6.2.2 Pyrrolidine alkaloids.- 6.3 Isoquinoline and related alkaloids.- 6.3.1 Phenethylamines and simple isoquinolines.- 6.3.2 Aporphines.- 6.3.3 Erythrina alkaloids.- 6.3.4 Morphine and related alkaloids.- 6.3.5 Hasubanonine and protostephanine.- 6.3.6 Protoberberine and related alkaloids.- 6.3.7 Phenethylisoquinoline alkaloids.- 6.4 Amaryllidaceae and mesembrine alkaloids.- 6.4.1 Amaryllidaceae alkaloids.- 6.4.2 Mesembrine alkaloids.- 6.5 Quinoline and related alkaloids.- 6.6 Indole alkaloids.- 6.6.1 Simple indole derivatives.- 6.6.2 Terpenoid indole and related alkaloids.- 6.7 Ipecac alkaloids.- 6.8 Miscellaneous alkaloids.- References.- 7 Microbial metabolites containing nitrogen.- 7.1 Introduction.- 7.2 Piperidine and pyridine metabolites.- 7.3 Diketopiperazines.- 7.4 Benzodiazepines.- 7.5 Metabolites derived from the tryptophan pathway.- 7.5.1 Ergot alkaloids.- 7.5.2 Cyclopiazonic acids and carbazomycin B.- 7.5.3 Indolmycin.- 7.5.4 Streptonigrin and pyrrolnitrin.- 7.6 Metabolites derived from the shikimate pathway.- 7.6.1 Pseudans, phenoxazinones, phenazines, and chloramphenicol.- 7.6.2 Ansamycins, mitomycins and antibiotic A23187.- 7.6.3 Cytochalasins and pseurotin A.- 7.6.4 Nybomycin.- 7.6.5 Naphthyridinomycin, saframycin A and CC-1065.- 7.6.6 Isocyanides and tuberin.- 7.6.7 Sarubicin A.- 7.6.8 Arphamenines.- 7.7 ?-Lactams.- 7.7.1 Penicillins and cephalosporins.- 7.7.2 Clavulanic acid.- 7.7.3 Nocardicins.- 7.7.4 Thienamycin and tabtoxin.- 7.8 Miscellaneous metabolites.- 7.8.1 Prodiginines.- 7.8.2 Elaiomycin and valinimycin.- 7.8.3 Streptothricin, acivicin, reductiomycin and asukamycin.- 7.8.4 Myxopyronin A, myxothiazol, angiolam A, rhizoxin and malonimycin.- 7.8.5 Virginiamycin antibiotics.- 7.8.6 Cyclizidine.- References.
226 citations
TL;DR: With this newly established methodology, asymmetric total synthesis of (-)-Mesembrine in high enantiomeric excess (98% ee) was accomplished.
Abstract: Desymmetrization of cyclohexadienones via aza-Michael reaction catalyzed by cinchonine derived thiourea has been realized to afford a series of highly enantioenriched pyrrolidine and morpholine derivatives in excellent yields and ees. With this newly established methodology, asymmetric total synthesis of (-)-Mesembrine in high enantiomeric excess (98% ee) was accomplished.
171 citations
TL;DR: An unusual additive effect with DMAP has been uncovered that allows for altered reactivity and the formation of quaternary carbon centers in isoprene and its derivatives.
Abstract: A method for the regioselective arylboration of isoprene and its derivatives is presented. These reactions allow for the synthesis of useful building blocks from simple components. Through these studies, an unusual additive effect with DMAP has been uncovered that allows for altered reactivity and the formation of quaternary carbon centers. The utility of this method is demonstrated toward the formal synthesis of mesembrine.
121 citations
TL;DR: The activity of the Sceletium tortuosum extract on the 5-HT transporter and PDE4 may explain the clinical effects of preparations made from this plant, and relate to the presence of alkaloids, particularly mesembrine and mesembrenone.
120 citations
TL;DR: In this paper, the Sceletium alkaloid (−)-mesembrine was synthesized in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34 percent yield from ethyl 3-bromopropionate).
Abstract: An efficient, total synthesis of the Sceletium alkaloid (−)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexanol as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.
90 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2021 | 3 |
| 2019 | 1 |
| 2018 | 3 |
| 2017 | 4 |
| 2016 | 9 |
| 2015 | 4 |