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A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Author(s) -
Zhou Shiqiang,
Tong Rongbiao
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601245
Subject(s) - total synthesis , catalysis , chemistry , catalytic hydrogenation , combinatorial chemistry , group (periodic table) , stereochemistry , organic chemistry
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 PtO 2 ‐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.