folicanthine has been researched along with chimonanthine* in 7 studies
7 other study(ies) available for folicanthine and chimonanthine
| Article | Year |
|---|---|
FeCl
An FeCl Topics: Allyl Compounds; Catalysis; Chlorides; Ferric Compounds; Indoles; Molecular Structure; Oxindoles; Pyrroles; Stereoisomerism | 2017 |
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 |
Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821.
While metal-promoted activation of tertiary alkyl halides often causes elimination and hydrodehalogenation, we have developed a nickel-catalyzed reductive dimerization that allows the generation of a potently reactive tertiary radical equivalent to form a very congested C(sp(3))-C(sp(3)) bond even below room temperature. The catalytic protocol is applicable to the dimerization of several pyrrolidinoindoline scaffolds through an appropriate choice of catalyst to accommodate different substrate reactivities with functional group compatibilities. The efficiency of the nickel-catalyzed protocol was successfully demonstrated through a systematic total synthesis of chimonanthines, folicanthines and (+)-WIN 64821. Topics: Catalysis; Dimerization; Indoles; Molecular Structure; Nickel; Piperazines; Pyrroles; Stereoisomerism | 2014 |
Ni-catalyzed reductive homocoupling of unactivated alkyl bromides at room temperature and its synthetic application.
A room-temperature Ni-catalyzed reductive approach to homocoupling of unactivated primary, secondary, and tertiary alkyl bromides is described. The catalytic system can be easily generated from air-stable and cheap materials and demonstrates broad functional group tolerance, thus allowing facile access to useful dimeric triterpene and lignan-like molecules. Moreover, the dimerization of tertiary bromide 6 efficiently establishes sterically hindered vicinal quaternary carbons (C3a and C3a'), which is a key linkage of intriguing bispyrrolo[2,3-b]indoline alkaloids, thereby enabling us to complete the total syntheses of racemic chimonanthine (9) and folicanthine (10). In addition, this dimerization method can be expanded to the highly stereoselective synthesis of bisperhydrofuro[2,3-b]furan (5a) and the dimeric spiroketal 5b, signifying the involvement of possible radical species. Topics: Bromides; Catalysis; Dimerization; Furans; Hydrocarbons, Brominated; Indoles; Molecular Structure; Nickel; Pyrroles; Stereoisomerism; Temperature | 2013 |
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 |