70614-67-4Relevant articles and documents
Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids
Schrittwieser, Joerg H.,Resch, Verena,Wallner, Silvia,Lienhart, Wolf-Dieter,Sattler, Johann H.,Resch, Jasmin,MacHeroux, Peter,Kroutil, Wolfgang
, p. 6703 - 6714 (2011/10/18)
A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.
Synthesis of (+/-)-Isoboldine and (+/-)-2'-Amino and Nitro Derivatives of Reticuline and Laudanidine
Bhakuni, D. S.,Kumar, Parveen
, p. 1027 - 1030 (2007/10/02)
(+/-)-2'-Nitro and amino derivatives of reticuline and laudanidine and aporphine alkaloid, isoboldine have been synthesized.Pschorr cyclisation of (+/-)-2'-amino-O,O'-dibenzylreticuline yields (+/-)-O,O'-dibenzylisoboldine, O,O'-dibenzylreticuline and O-b
Synthesis of alkaloids using Reissert compounds, II. A new synthesis of (±)-reticuline (Preliminary communication)
Kerekes,Makleit,Bognar
, p. 491 - 493 (2007/10/05)
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