109374-24-5Relevant academic research and scientific papers
Preparation of 8-methylberberines and aza analogues: Synthesis of (+/-)-alamandrine
MacLean, Jahangir,MacLean, David B.,Holland, Herbert L.
, p. 727 - 733 (2007/10/02)
Methyllithium reacted with oxyberberine, affording on alkaline work-up a compound with an exomethylene group at C-8 that was transformed in acidic media into an 8-methylberberinium salt.The iminium salt was reduced to a mixture of racemic α- and β-8-methylcanadine. 5,6-Dihydro-8H-isoquinonaphthyridin-8-ones were similarly transformed into 8-exo-methylene and 8-methyl derivatives, which were subjected to further reduction.These reactions have been employed in a synthesis of the Alangium alkaloid, (+/-)-alamandrine.
Activated Imines as Carbon Electrophiles: Applications in Alkaloid Synthesis
Jahangir,MacLean, David B.,Brook, Michael A.,Holland, Herbert L.
, p. 1608 - 1609 (2007/10/02)
3,4-Dihydroisoquinolines and 3,4-dihydro-β-carbolines react with trimethylsilyl trifluoromethanesulphonate to form complexes that react readily with the lithio derivatives of 3-cyano-4-methylpyridines; the method has been applied to the synthesis of the Alangium alkaloids, (+/-)-alangimaridine and alangimarine.
