Pyrrolam A

CAS# 126424-76-8

Pyrrolam A

Catalog No. BCN2040----Order now to get a substantial discount!

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Quality Control of Pyrrolam A

Number of papers citing our products

Chemical structure

Pyrrolam A

3D structure

Chemical Properties of Pyrrolam A

Cas No. 126424-76-8 SDF Download SDF
PubChem ID 5325756 Appearance Cryst.
Formula C7H9NO M.Wt 123.15
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8R)-5,6,7,8-tetrahydropyrrolizin-3-one
SMILES C1CC2C=CC(=O)N2C1
Standard InChIKey FVZBHZCORGROSI-ZCFIWIBFSA-N
Standard InChI InChI=1S/C7H9NO/c9-7-4-3-6-2-1-5-8(6)7/h3-4,6H,1-2,5H2/t6-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Pyrrolam A

In vitro

Synthesis of (R)‐(‐)‐Pyrrolam A (I) and Studies on Its Stability: A Caveat on Computational Methods[Reference: WebLink]

The Journal of Organic Chemistry,2004, 69(18):6105-14.

The asymmetric synthesis of (-)-(R)-Pyrrolam A was achieved in three operations from N-Boc pyrrolidine via an alpha-(N-carbamoyl)alkylcuprate vinylation reaction followed by N-Boc deprotection and cyclization. One-pot deprotection-cyclization procedures led to mixtures of Pyrrolam A and its double bond isomers. These isomerization events could be circumvented by use of a two-step procedure.
METHODS AND RESULTS:
To guide aspects of the experiments, a series of computational energy evaluations and chemical shift predictions were performed with molecular mechanics, semiempirical, ab initio, and density functional methods. The relative stabilities of the double bond isomers, as estimated by experiment, challenged a number of computational methods, and only the MP2 model with its moderate degree of electron correlation came close to matching the experimental data. The MP2 method was further applied to an unusual aspect of the double bond migration between Pyrrolam A and its isomer 9.
CONCLUSIONS:
The reaction (1 to 9) on neat samples is irreversible without racemization, and the alumina-mediated equilibration is accompanied by complete loss of enantiomeric excess. The source of the irreversibility was traced to asymmetric charge distribution in the intermediate dienolate anion. The analysis ultimately led to a semiquantitative sketch of the pyrrolam energy surface.

Protocol of Pyrrolam A

Structure Identification
Org Lett. 2014 Jul 18;16(14):3780-3.

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: synthesis of (R)-pyrrolam A.[Pubmed: 24972082]


METHODS AND RESULTS:
A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity.
CONCLUSIONS:
Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product Pyrrolam A.

Tetrahedron,1996,52(3): 869–876.

First total synthesis of pyrrolam A.[Reference: WebLink]


METHODS AND RESULTS:
First synthesis of Pyrrolam A (1), a pyrrolizidine alkaloid from Streptomyces olivaceus, was accomplished. The SmI2-mediated intramolecular coupling reaction between a bromoalkyl and ynamide group gave solely a cyclized product, which was converted to Pyrrolam A (1) efficiently.

Pyrrolam A Dilution Calculator

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Pyrrolam A Molarity Calculator

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Preparing Stock Solutions of Pyrrolam A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 8.1202 mL 40.6009 mL 81.2018 mL 162.4036 mL 203.0045 mL
5 mM 1.624 mL 8.1202 mL 16.2404 mL 32.4807 mL 40.6009 mL
10 mM 0.812 mL 4.0601 mL 8.1202 mL 16.2404 mL 20.3004 mL
50 mM 0.1624 mL 0.812 mL 1.624 mL 3.2481 mL 4.0601 mL
100 mM 0.0812 mL 0.406 mL 0.812 mL 1.624 mL 2.03 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Pyrrolam A

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: synthesis of (R)-pyrrolam A.[Pubmed:24972082]

Org Lett. 2014 Jul 18;16(14):3780-3.

A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product Pyrrolam A.

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