Boron-Selective Biaryl Coupling Approach to Versatile Dibenzoxaborins and Application to Concise Synthesis of Defucogilvocarcin M

Yuto Sumida^†, Ryu Harada^†, Tomoe Kato-Sumida^†, Kohei Johmoto^‡, Hidehiro Uekusa^‡, and Takamitsu Hosoya^*^†

^† Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

^‡ Department of Chemistry and Materials Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8551, Japan

Org. Lett., 2014, 16 (23), pp 6240–6243

DOI: 10.1021/ol5031734

Publication Date (Web): November 24, 2014

Copyright © 2014 American Chemical Society

*E-mail: thosoya.cb@tmd.ac.jp.

Abstract

Abstract Image

An efficient synthetic method for versatile dibenzoxaborins based on boron-selective Suzuki–Miyaura cross-coupling between o-borylphenols and aryl halides or triflates bearing a 1,8-diaminonaphthalene-protected o-boryl group is reported. A short synthesis of defucogilvocarcin M was achieved using the proposed method in combination with several other boron-mediated transformations.

Supporting Information

Experimental procedures and characterization data including copies of NMR spectra and the X-ray crystallographic data. This material is available free of charge via the Internet at http://pubs.acs.org.

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