6533b834fe1ef96bd129e2f1
RESEARCH PRODUCT
A one-pot cascade to protoberberine alkaloids via Stevens rearrangement of nitrile-stabilized ammonium ylides.
Jan-gernot DeichmannGuenther LahmTill OpatzAnna Lisa Rauensubject
PseudopalmatineNitrileMolecular StructureOrganic ChemistryBerberine Alkaloidschemistry.chemical_compoundAlkaloidschemistryStevens rearrangementCascadeTetrahydroisoquinolinesAmmonium CompoundsNitrilesOrganic chemistryMoleculeAmmoniumProtecting groupdescription
A facile one-pot synthesis of protoberberines from readily accessible 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles and 1,2-bis(bromomethyl)arenes is described. The reaction cascade comprises four consecutive transformations, all of which can be effected under a single set of conditions. Ten protoberberines, including the alkaloids pseudopalmatine and pseudoepiberberine, were prepared in yields up to 86% according to this strategy. No chromatographic purification of the products is required, and the route is devoid of any protecting group manipulations.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-01-27 | The Journal of organic chemistry |