Anionic Fries rearrangements of esters of ortho-iodobenzyl alcohols: rapid routes to oestrone methyl ether and its 9β epimer, and aryl naphthalide lignans
Abstract
A fast, general, low-temperature rearrangement of ortho-iodobenzyl esters, triggered by lithium–iodine exchange, leads to isobenzofurans which are intercepted in situ by inter and intramolecular Diels–Alder (IMDA) reactions to produce a variety of carbocycles including natural lignans and steroids.