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Regioselective Biomimetic Oxidative Cyclization Strategy for the Synthesis of Aryldihydronaphthalene Lignans
Author(s) -
Li Wenling,
Liu Hao,
Xu Jingyan,
Zang Peng,
Liu Qian,
Li Wenbo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301825
Subject(s) - regioselectivity , chemistry , oxidative coupling of methane , oxidative phosphorylation , biomimetic synthesis , tetrahydrofuran , catalysis , combinatorial chemistry , organic chemistry , biochemistry , solvent
A regioselective biomimetic oxidative cyclization strategy for the construction of aryldihydronaphthalene skeletons has been developed as an efficient synthetic approach to the preparation of natural 8‐8‐cyclic diferulic acid and canabisin D. The oxidative coupling of ethyl 5‐ tert ‐butylferulate catalyzed by different oxidants yielded tetrahydrofuran or dibenzylidenesuccinate‐type 8‐8‐coupling products, which were subsequently subjected to acid‐catalyzed cyclization to produce several isomeric trans ‐aryldihydronaphthalenes. The reaction mechanisms for all the cyclization reactions have also been proposed.