Ferrugine
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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Tetrahedron,2012,68(39): 8236–8244.
Approaches to the enantioselective synthesis of ferrugine and its analogues[Reference:
WebLink]
A four-step synthetic route, to Ferrugine (2α-benzoyltropane), its methyl analogue (2-acetyltropane) and their N-benzyl analogues is reported.
METHODS AND RESULTS:
The reaction sequence uses tropinone or N-benzylnortropinone aldols as key intermediates. Reduction of aldol derived N-tosylhydrazones and oxidation of the side chain hydroxyl group followed by spontaneous diastereomer equilibration provides the final products. Relative configuration of the exo,anti N-methyl and N-benzyl aldols was retained during N-tosylhydrazone formation. The relative stereochemistry of N-tosylhydrazones was assigned by single crystal diffraction.
CONCLUSIONS:
The final products, Ferrugine and its methyl analogue, were synthesized in enantiomerically pure form via asymmetric deprotonation of tropinone using chiral lithium amide/lithium chloride aggregate prepared in situ from (S,S)-N,N-bis(1-phenylethyl)amine hydrochloride.
Tetrahedron Letters,2009,50(51):7196–7198.
Enantioselective route to ferrugine and its methyl analogue via aldol deoxygenation[Reference:
WebLink]
A simple enantioselective approach to Ferrugine (2α-benzoyltropane) and its methyl analogue (2-acetyltropane) is reported.
METHODS AND RESULTS:
The four-step sequence uses an enantioselective aldol reaction of tropinone with benzaldehyde or acetaldehyde, combined with an aldol deoxygenation via tosylhydrazone reduction and oxidation of the side-chain hydroxy group. The final products, Ferrugine and its methyl analogue, are prepared in 35% and 23% overall yields, respectively.
CONCLUSIONS:
Both enantiomers of the products (ee 90–99%) are accessible via the same route using either enantiomer of N,N-bis(1-phenylethyl)amine hydrochloride as the chiral reagent.
