Issue 2, 1992

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1992, 164-166

Anionic Fries rearrangements of esters of ortho-iodobenzyl alcohols: rapid routes to oestrone methyl ether and its 9β epimer, and aryl naphthalide lignans

S. Horne and R. Rodrigo, J. Chem. Soc., Chem. Commun., 1992, 164 DOI: 10.1039/C39920000164

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