Russell Rodrigo

A regiocontrolled synthesis of some arylnaphthalide ligans

Three arylnaphthalide ligands are synthesised by regiocontrolled transformations of Diels–Alder adducts generated from dimethyl acetylenedicarboxylate and suitable isobenzofurans.

Preparation, properties, and some chemical reactions of phenaleno[1,9-bc]furan

The synthesis of hitherto unknown phenaleno[1,9-bc]furan (1), in 11% overall yield from 2-naphthol, has been achieved. Its 1H and 13C n.m.r. spectra have been fully assigned by means of heteronuclear 2D correlations. The furanoid moiety of (1) displays Diels–Alder diene reactivity in its reactions with benzyne, dimethyl acetylenedicarboxylate, and singlet oxygen. The furan ring of (1) also suffers oxidation by m-chloroperbenzoic acid and undergoes catalytic hydrogenation. This chemistry appears to be more characteristic of naphtho[1,2-c]furan than of naphtho[1,2-b]furan although both structural units co-exist in structure (1).

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

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.

A short efficient route to acronycine and other acridones

A Fries type of rearrangement of N-tosyl-o-iodobenzanilides, triggered by lithium–iodine exchange at low temperature is the key step in a general, regiospecific synthesis of acridones.