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DOI: 10.1039/A702992F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2707-2712

Applications of the spiroannulation of tetralins with alkynes; towards new anti-estrogenic compounds

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F. Thomas Boyle, Owen Hares, Zbigniew S. Matusiak, Warren Li and Donald A. Whiting

Abstract

Thermal reaction of the benzocyclobutene 17 with 4-methoxystyrene leads to 1-cyano-2-(4-methoxyphenyl)-6-methoxytetralin[hair space]† 19 through an electrocyclic ring opening Diels–Alder sequence: the derived acid chloride 20, and its analogue 10, then undergoes an unusual addition–cyclisation reaction with alkynes catalysed by aluminium chloride, to yield the tricyclospirodienones 21a–c and 11a,b; the former set show moderate aromatase inhibitory activity.

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