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- Title
Regioselective Biomimetic Oxidative Cyclization Strategy for the Synthesis of Aryldihydronaphthalene Lignans.
- Authors
Li, Wenling; Liu, Hao; Xu, Jingyan; Zang, Peng; Liu, Qian; Li, Wenbo
- Abstract
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.
- Subjects
BIOMIMETIC polymers; RING formation (Chemistry); OXIDATIVE coupling; OXIDIZING agents; TETRAHYDROFURAN
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 16, p3475
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301825