Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products
نویسندگان
چکیده
Described herein is a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The method was based on detailed knowledge reaction mechanisms in order develop robust conditions toward selective synthesis either or products. In this frame, we exploited ability HFIP stabilize radical cation intermediates activate oxidants flow such as glaucine, rogersine nantenine. On other hand, established that PhI(OAc)(OTf), prepared by action TMSOTf PhI(OAc)2, powerful oxidant sebiferine amurine.
منابع مشابه
Aporphine Alkaloids as Ligands for Serotonin Receptors
The aporphine alkaloids are known to have affinities as the dopaminergic, adrenergic and serotonergic receptor system. Hence the aporphine template can be considered as a privileged scaffold for the design of selective monopotent as well as multi-potent Central Nervous System (CNS) ligands. This review attempts to summarize the recent Structure Activity Relationship (SAR) studies of aporphine a...
متن کاملAPORPHINE ALKALOIDS FROM Ocotea macrophylla (LAURACEAE)
Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae) were isolated and characterized as (S)-3-methoxynordomesticine (1), (S)-N-ethoxycarbonyl-3-methoxy-nordomesticine (2), (S)-N-formyl-3-methoxy-nordomesticine (3) and (S)N-methoxycarbonyl-3-methoxy-nordomesticine (4); alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined base...
متن کاملNatural aristolactams and aporphine alkaloids as inhibitors of CDK1/cyclin B and DYRK1A.
In an effort to find potent inhibitors of the protein kinases DYRK1A and CDK1/Cyclin B, a systematic in vitro evaluation of 2,500 plant extracts from New Caledonia and French Guyana was performed. Some extracts were found to strongly inhibit the activity of these kinases. Four aristolactams and one lignan were purified from the ethyl acetate extracts of Oxandra asbeckii and Goniothalamus dumont...
متن کاملNew cytotoxic tetrahydroprotoberberine-aporphine dimeric and aporphine alkaloids from Corydalis turtschaninovii.
Two new tetrahydroprotoberberine-aporphine dimeric alkaloids, corydaturtschines A (1) and B (2), and a new aporphine derivative, ethyl glausuccinate (3), together with 13 known protoberberine (4-16) and nine known aporphine alkaloids (17-25), were isolated from the tubers of Corydalis turtschaninovii. The structures of these new compounds were determined through spectral analyses, including ext...
متن کاملThe Cyclization of Natural Rubber
The effects of solvent, temperature, time, weight percent of catalyst on the rate and mechanism of cyclization of natural rubber (NR) was studied in toluene and xylene solutions having tin tetra chloride catalyst (SnCl4). Iodometric titration show, with 8% SnCl4 (based on polymer weight) cyclization occurs, leaving 27.4% of the total unsaturation. Infrared spectra of c...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: European Journal of Organic Chemistry
سال: 2022
ISSN: ['1434-193X', '1099-0690']
DOI: https://doi.org/10.1002/ejoc.202200301