A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps - PubMed (original) (raw)
. 2016 May 17;22(21):7084-9.
doi: 10.1002/chem.201601245. Epub 2016 Apr 23.
Affiliations
- PMID: 26990887
- DOI: 10.1002/chem.201601245
A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Shiqiang Zhou et al. Chemistry. 2016.
Abstract
A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A(3) reaction, Pd-catalyzed reductive carbocyclization, and PtO2 -catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
Keywords: 13-methylprotoberberine; aporhoeadane; protoberberine; redox-A3 reaction; total synthesis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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