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Review | Special issue | Vol 79, No. 1, 2009, pp.243-263
Published online, 22nd December, 2008
DOI: 10.3987/REV-08-SR(D)9
3-Methyl-2,5-dihydro-1-benzoxepins and 3-Methyl-2,5-dihydrooxepins

Seiji Yamaguchi*

*Department of Chemistry, Graduate School of Science and Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan

Abstract

Three preparative procedures of seven-membered O-heterocyclic 3-methyl-2,5-dihydro-1-benzoxepin derivatives are summarized. For the Z-selective formation of C=C double bond, the first approach used the Grubbs ring-closing methathesis, the second approach used the intramolecular Mitsunobu cyclization of corresponding Z-diols prepared using Stille coupling of the benzyl bromide with (Z)-vinylstannane, and the third approach used the revised synthesis of the Z-diols using Z-selective Ando-Horner-Emmons condensation and the following DIBAL-H reduction. Some naturally occurring 3-methyl- 2,5-dihydro-1-benzoxepin derivatives were synthesized using these procedures. In these studies, some preparations of 3-methyl-2,5-dihydrooxepin derivatives were also developed.