Pyrrolam A
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.
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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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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.
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.
