Pyrrolam A | CAS:126424-76-8 | Manufacturer ChemFaces

Pyrrolam A

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Description:

Reference standards.

In vitro:

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

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

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.

Pyrrolam A Description

Source:	From Streptomyces olivaceus.
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. 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.

Product Name	Pyrrolam A
Price:
CAS No.:	126424-76-8
Catalog No.:	CFN00328
Molecular Formula:	C₇H₉NO
Molecular Weight:	123.15 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Cryst.
Source:	From Streptomyces olivaceus.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
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	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

CFN00279	Trachelanthamidine	526-64-7	141.21	C₈H₁₅NO
CFN00280	Laburnine	3348-73-0	141.21	C₈H₁₅NO
CFN00281	Isoretronecanol	526-63-6	141.21	C₈H₁₅NO
CFN00296	Loroquine	27792-82-1	151.16	C₈H₉NO₂
CFN95293	3-Oxo-4-benzyl-3,4-dihydro-1H-pyrrolo [2,1-c] oxazine-6-methylal	60026-28-0	255.3	C₁₅H₁₃NO₃
CFN00328	Pyrrolam A	126424-76-8	123.15	C₇H₉NO
CFN00248	Clazamycin B	71774-49-7	172.61	C₇H₉ClN₂O
CFN00250	Crotanecine	5096-50-4	171.20	C₈H₁₃NO₃
CFN00252	Danaidal	27628-46-2	135.16	C₈H₉NO
CFN00253	Danaidone	6064-85-3	135.16	C₈H₉NO