Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 16, Pages 6703-6714Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201056f
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Funding
- Austrian Science Fund [P20903-N17, P22115-N17]
- NAWI Graz
- Austrian Science Fund (FWF) [W 901] Funding Source: researchfish
- Austrian Science Fund (FWF) [P20903, P22115] Funding Source: Austrian Science Fund (FWF)
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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)-benzyl- isoquinoline 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-C alpha 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.
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