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J Org Chem. 2017 Mar 17;82(6):3317-3326. doi: 10.1021/acs.joc.7b00108. Epub 2017 Mar 7.

Synthesis of Substituted 1,6-Diarylnaphthalenes via a Tandem Claisen Rearrangement and Ene Reaction Protocol.

Author information

1
Department of Medicinal and Applied Chemistry, General Research Centers of R&D office, Kaohsiung Medical University Hospital, Kaohsiung Medical University , Kaohsiung 807, Taiwan.

Abstract

In this work, we developed a concise synthetic route for the synthesis of polysubstituted naphthalenes starting from commercially available isovanillin and its derivatives. Reaction with styryl bromide via O-styrylation, Claisen rearrangement, ene reaction, and O-alkylation occurred in high yields. The key structures were confirmed by single-crystal X-ray diffraction.

PMID:
28248498
DOI:
10.1021/acs.joc.7b00108

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