Total Synthesis of (−)‐Jiadifenin | Zendy

Yang Yang | Zendy; Fu Xingnian | Zendy; Chen Jianwei | Zendy; Zhai Hongbin | Zendy

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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.

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