Reversal of the regioselectivity in a cycloaddition of o-quinones by varying the position of alkoxy substituents

A. Kuboki, T. Yamamoto, M. Taira, T. Arishige, R. Konishi, M. Hamabata, M. Shirahama, T. Hiramatsu, K. Kuyama, S. Ohira

We have investigated the regioselective cycloaddition of o-quinones with the protected sinapyl alc. I. It was found that the position of the alkoxy substituent on the o-quinone ring controlled the regioselectivity of the cycloaddition In addition, our reported procedure for determining the location of the side chains on 1,4-benzodioxanes, e.g. II, has been improved.

Tetrahedron Letters

Elsevier Ltd.

49

16

2558

2561