Tetrahedron letters

The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

CD Gabbutt, JD Hepworth, BM Heron, JL Thomas

Index: Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark; Thomas, Jean-Luc Tetrahedron Letters, 1998 , vol. 39, # 8 p. 881 - 884

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Citation Number: 23

Abstract

ABSTRACT: Syntheses of dehydrorotenoid and benzoxanthone units from 2′- hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.

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