A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and RCM.

A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement of a (Z)-3-alkoxyprop-2-en-1-yl glycolate ester having a cyclic ether on the oxygen at C3 of the (Z)-prop-2-en-1-yl group stereoselectively produced an anti-alpha,beta-dialkoxyester, which was successfully transformed to a fused bicyclic ether via a reaction sequence including RCM.