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Communication | Regular issue | Vol 23, No. 3, 1985, pp.553-556
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0553
Synthesis of Substituted Tetrahydrofurans and Tetrahydropyrans 1. Oxidative Cyclization of p-Methoxystyrene Derivatives with DDQ

Yuji Oikawa, Kiyoshi Horita, and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

In the course of synthetic studies of polyether antibiotics, we tried to develop a new synthetic method of substituted tetrahydrofuran and tetrahydropyran rings. When p-methoxystyrene derivatives having a hydroxy group at a suitable position was treated with DDQ, an oxidative cyclization of E-olefins, not Z-olefins, occurred yielding substituted tetrahydrofurans and tetrahydropyrans, though in low yields.