Isodomoic acid G | CAS:188346-81-8 | Manufacturer ChemFaces

Isodomoic acid G

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Description:

Reference standards.

In vitro:

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.

Isodomoic acid G Description

Source:	From Chondria armata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	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
After receiving:	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.

Structure Identification:

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.

Product Name	Isodomoic acid G
Price:
CAS No.:	188346-81-8
Catalog No.:	CFN00119
Molecular Formula:	C₁₅H₂₁NO₆
Molecular Weight:	311.33 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	From Chondria armata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.212 mL	16.0601 mL	32.1203 mL	64.2405 mL	80.3006 mL
5 mM	0.6424 mL	3.212 mL	6.4241 mL	12.8481 mL	16.0601 mL
10 mM	0.3212 mL	1.606 mL	3.212 mL	6.4241 mL	8.0301 mL
50 mM	0.0642 mL	0.3212 mL	0.6424 mL	1.2848 mL	1.606 mL
100 mM	0.0321 mL	0.1606 mL	0.3212 mL	0.6424 mL	0.803 mL

CFN00117	Fuligorubin A	108343-55-1	357.40	C₂₀H₂₃NO₅
CFN00118	Harzianic acid	157148-06-6	365.42	C₁₉H₂₇NO₆
CFN00119	Isodomoic acid G	188346-81-8	311.33	C₁₅H₂₁NO₆
CFN00120	Janolusimide	103612-45-9	383.49	C₁₉H₃₃N₃O₅
CFN00124	Malonomicin	38249-71-7	374.31	C₁₃H₁₈N₄O₉
CFN00125	Nocamycin I	78339-49-8	503.55	C₂₆H₃₃NO₉
CFN00133	Pramanicin	154445-05-3	369.46	C₁₉H₃₁NO₆
CFN00134	Preapiodionene	142808-39-7	269.30	C₁₃H₁₉NO₅
CFN00135	Reutericyclin	303957-69-9	349.47	C₂₀H₃₁NO₄
CFN90372	Broussonetine A	173220-07-0	507.62	C₂₄H₄₅NO₁₀