3122-95-0Relevant academic research and scientific papers
Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile
Blank, Nancy,Opatz, Till
, p. 9777 - 9784 (2012/01/30)
Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline- 1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines ( - )-corytenchine and ( - )-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.
The biosynthesis of papaverine proceeds via (S)-reticuline
Han, Xu,Lamsh?ft, Marc,Grobe, Nadja,Ren, Xuan,Fist, Anthony J.,Kutchan, Toni M.,Spiteller, Michael,Zenk, Meinhart H.
experimental part, p. 1305 - 1312 (2011/04/22)
Papaverine is one of the earliest opium alkaloids for which a biosynthetic hypothesis was developed on theoretical grounds. Norlaudanosoline (=tetrahydropapaveroline) was claimed as the immediate precursor alkaloid for a multitude of nitrogen containing p
Novel Biogenetic Pathways from (+)-Reticuline. Three Dimeric Alkaloids: (+)-Vanuatine, (+)-Vateamine, and (+)-Malekulatine
Bruneton, Jean,Shamma, Maurice,Minard, Robert D.,Freyer, Alan J.,Guinaudeau, Helene
, p. 3957 - 3960 (2007/10/02)
The bark of Hernandia peltata Meissner (Hernandiaceae), gathered in the Republic of Vanuatu (New Hebrides), has yielded the bis(benzylisoquinolines) (+)-vanuatine (5), (+)-vateamine (6), and (+)-malekulatine (7).These are the first-known dimers of (+)-reticuline (2).Compounds 5 and 6 are products of tail-to-tail oxidative coupling, whereas 7 involves head-to-tail coupling.
