Anionic Fries rearrangements of esters of ortho-iodobenzyl alcohols: rapid routes to oestrone methyl ether and its 9? epimer, and aryl naphthalide lignans
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 164-166
- https://doi.org/10.1039/c39920000164
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.Keywords
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