Calyciphylline A
Standard reference
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Chem Asian J. 2015 Apr;10(4):865-8.
Expedient construction of the [5-6-7] tricyclic core of calyciphylline a-type alkaloids.[Pubmed:
25377776]
METHODS AND RESULTS:
An efficient synthetic route toward the highly congested [5-6-7] tricyclic core of Calyciphylline A-type alkaloids has been developed. This approach features a highly efficient intramolecular Diels-Alder cycloaddition to establish the aza-five-membered C ring as well as the C1 all-carbon quaternary center, and a subsequent cyclopropanation together with a ring-expansion reaction of the resulted adduct to construct the seven-membered D ring.
Tetrahedron Lett. 2015 Jun 3;56(23):3503-3506.
Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations.[Pubmed:
26028785]
The Daphniphyllum alkaloids remain an attractive target in the synthetic community because of their unique framework and promising biological activities.
METHODS AND RESULTS:
We have shown that the ABC core of the Calyciphylline A-type alkaloids can be rapidly accessed via the tandem cyclization of a neutral aminyl radical with a polarized cyclic olefin. Deuterium labeling experiments and reactions omitting a tin hydride reagent suggest that the solvent is the major source of the terminating hydrogen atom in the cyclization cascade.
CONCLUSIONS:
Incorporation of an internal alkyne in the radical pathway was tolerated in the reaction, and it provided the necessary atoms to enable completion of the D ring of the Calyciphylline A-type alkaloids.
Org Lett. 2014 Feb 21;16(4):1072-5.
Rapid access to the heterocyclic core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids via tandem cyclization of a neutral aminyl radical.[Pubmed:
24506430]
A streamlined approach to the tertiary amine-containing core of the Calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids is presented.
METHODS AND RESULTS:
A known carvone derivative is converted into the core structure in only four synthetic operations, and it is well poised for further elaboration. The key enabling methodology is a radical cyclization cascade beginning with addition of a secondary, neutral aminyl radical to the β-position of an enone, followed by trapping with a pendant alkyne.
