jo201871c_si_001.pdf (5.74 MB)
Enantioselective Synthesis of Tetrahydroprotoberberines and Bisbenzylisoquinoline Alkaloids from a Deprotonated α-Aminonitrile
journal contribution
posted on 2011-12-02, 00:00 authored by Nancy Blank, Till OpatzUnder 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.
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nonracemic precursorsAminonitrileUnderdeprotonatedarmepavinealkaloidsTetrahydroprotoberberineBisbenzylisoquinoline AlkaloidsdimethoxylaudanidinetetrahydroprotoberberinetetrahydropseudoepiberberinemateriallaudanosineNoyoridihydroisoquinolineUllmann diaryl ether synthesesDeprotonateddimericpreparationtransfer hydrogenationtetramethylmagnolaminealkylationEnantioselective Synthesiscorytenchine
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