calycanthine and folicanthine

calycanthine has been researched along with folicanthine* in 5 studies

Other Studies

5 other study(ies) available for calycanthine and folicanthine

ArticleYear
Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine.
    The Journal of organic chemistry, 2015, Oct-16, Volume: 80, Issue:20

    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.
    Chemistry (Weinheim an der Bergstrasse, Germany), 2015, Nov-23, Volume: 21, Issue:48

    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.
    Angewandte Chemie (International ed. in English), 2012, May-21, Volume: 51, Issue:21

    Topics: Catalysis; Indoles; Naphthyridines; Pyrroles; Stereoisomerism

2012
Antifungal activity of alkaloids from the seeds of Chimonanthus praecox.
    Chemistry & biodiversity, 2009, Volume: 6, Issue:6

    Two alkaloids, D-calycanthine (1) and L-folicanthine (2), were isolated from the active MeOH extract of the seeds of Chimonanthus praecox LINK. The structures of the two compounds were established by (1)H- and (13)C-NMR, and MS (FAB, ESI) analyses. In the in vitro tests, compounds 1 and 2 showed significant inhibitory activities against five plant pathogenic fungi Exserohilum turcicum, Bipolaris maydis, Alternaria solani, Sclerotinia sderotiorum, and Fusarium oxysportium, among which B. maydis was found to be the most susceptible to 1 with an EC(50) value of 29.3 microg/ml, followed by S. sderotiorum to 2 with an EC(50) value of 61.2 microg/ml. To our knowledge, this is the first report of isolation and LC/MS/MS identification as well as of antifungal properties of these alkaloids from the seeds of this plant.

    Topics: Antifungal Agents; Calycanthaceae; Fungi; Indoles; Microbial Sensitivity Tests; Naphthyridines; Pyrroles; Seeds

2009
Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine.
    Angewandte Chemie (International ed. in English), 2007, Volume: 46, Issue:20

    Topics: Indoles; Molecular Conformation; Naphthyridines; Pyrroles; Stereoisomerism

2007