Isodomoic acid G
Reference standards.
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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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J Am Chem Soc. 2009 Dec 9;131(48):17714-8.
Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis.[Pubmed:
19899794]
METHODS AND RESULTS:
A unified approach to the pyrrolidine triacid natural products Isodomoic acid G and isodomoic acid H has been developed. Total syntheses of both natural products were completed, and determination of the correct stereostructure of Isodomoic acid G was established by comparing 5'-(R) and 5'-(S) isomers to a sample of authentic material. A nickel-catalyzed cyclization constructs the pyrrolidine ring while simultaneously establishing either the E or Z stereochemistry of an exocyclic tetrasubstituted alkene.
CONCLUSIONS:
Stereoselective assembly of both the E- and Z-alkenes of the natural products is made possible by a predictable strategy that alters the timing of substituent introduction to control alkene stereochemistry.
Org Lett. 2003 Oct 2;5(20):3771-3.
First total synthesis and stereochemical definition of isodomoic acid G.[Pubmed:
14507227]
METHODS AND RESULTS:
The first total synthesis and stereochemical definition of Isodomoic acid G has been achieved. The key nickel-catalyzed coupling of an alkynyl enone with an alkenylzirconium allows formation of the pyrrolidine ring and most of the stereochemical features in a single step.
CONCLUSIONS:
This report provides the first total synthesis application of this new reaction and illustrates its utility in the stereoselective preparation of highly substituted 1,3-dienes.
J Org Chem. 2011 Jan 7;76(1):201-15.
Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.[Pubmed:
21121685]
Marine neuroexcitatory compounds Isodomoic acid G and isodomoic acid H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction.
METHODS AND RESULTS:
A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to Isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.
