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Regioselective Oxidation Approaches to Concise Synthesis of (±)‐Canabisin D
Author(s) -
Li Wenling,
Liu Qian,
Liu Hao,
Chen Peilan,
Yang Xi,
Liu Yingying
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500054
Subject(s) - chemistry , regioselectivity , bromine , yield (engineering) , oxidative coupling of methane , acetone , oxidative phosphorylation , natural product , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , biochemistry , materials science , metallurgy
The regioselective effects of tert ‐butyl or bromine as the position‐protecting group of feruloytyamide on the oxidative coupling reactions for the synthesis of natural (±)‐canabisin D were investigated in detail. The coupling yield of 8‐8‐coupled aryldihydronaphthalene product of 5‐Br‐feruloytyamide was higher than that of tert ‐butyl substituted precursor under FeCl 3 ·6H 2 O‐acetone‐water oxidative condition.