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Total Synthesis of (−)‐Jiadifenin
Author(s) -
Yang Yang,
Fu Xingnian,
Chen Jianwei,
Zhai Hongbin
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203176
Subject(s) - quaternary carbon , intramolecular force , cycloaddition , chemistry , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , enantioselective synthesis
As easy as ABCD : (−)‐Jiadifenin was synthesized in eighteen reaction steps from 1‐[( E )‐(4′‐bromo‐2′‐butenyl)oxy]‐4‐methoxybenzene. Key features of this synthesis include: 1) Ireland–Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson–Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo‐cycloaddition to generate the all‐carbon quaternary center at C9.