calycanthine has been researched along with chimonanthine* in 5 studies
5 other study(ies) available for calycanthine and chimonanthine
| Article | Year |
|---|---|
Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.
While interest in the synthetic chemistry of radical cations continues to grow, controlling enantioselectivity in the reactions of these intermediates remains a challenge. Based on recent insights into the oxidation of tryptophan in enzymatic systems, we report a photocatalytic method for the generation of indole radical cations as hydrogen-bonded adducts with chiral phosphate anions. These noncovalent open-shell complexes can be intercepted by the stable nitroxyl radical TEMPO· to form alkoxyamine-substituted pyrroloindolines with high levels of enantioselectivity. Further elaboration of these optically enriched adducts can be achieved via a catalytic single-electron oxidation/mesolytic cleavage sequence to furnish transient carbocation intermediates that may be intercepted by a wide range of nucleophiles. Taken together, this two-step sequence provides a simple catalytic method to access a wide range of substituted pyrroloindolines in enantioenriched form via a standard experimental protocol from a common synthetic intermediate. The design, development, mechanistic study, and scope of this process are presented, as are applications of this method to the synthesis of several dimeric pyrroloindoline natural products. Topics: Biological Products; Catalysis; Cations; Cyclic N-Oxides; Hydrogen Bonding; Indole Alkaloids; Indoles; Naphthyridines; Phosphoric Acids; Pyrroles; Stereoisomerism | 2018 |
Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine.
Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (-)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (-)-calycanthine (3). Topics: Catalysis; Indole Alkaloids; Indoles; Molecular Structure; Naphthyridines; Pyrroles; Stereoisomerism | 2015 |
Catalytic Enantioselective Decarboxylative Allylations of a Mixture of Allyl Carbonates and Allyl Esters: Total Synthesis of (-)- and (+)-Folicanthine.
A highly enantioselective decarboxylative allylation of a mixture of enol carbonates and allyl esters has been achieved. The strategic viability of this methodology has been demonstrated through the total synthesis of cyclotryptamine alkaloids (-)- and (+)-folicanthine (1 a) and the formal total synthesis of (-)-chimonanthine (1 b), (+)-calycanthine (1 c), and (-)-ditryptophenaline (1 d). Topics: Allyl Compounds; Carbonates; Catalysis; Esters; Indoles; Molecular Structure; Naphthyridines; Pyrroles; Stereoisomerism | 2015 |
Catalytic asymmetric total synthesis of chimonanthine, folicanthine, and calycanthine through double Michael reaction of bisoxindole.
Topics: Catalysis; Indoles; Naphthyridines; Pyrroles; Stereoisomerism | 2012 |
Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine.
Topics: Indoles; Molecular Conformation; Naphthyridines; Pyrroles; Stereoisomerism | 2007 |