An approach toward isoindolobenzazepines using the ammonium ylide/Stevens [1, 2]-rearrangement sequence

…, LS Beall, CK Eidell, KJ Worsencroft

Index: Padwa; Beall; Eidell; Worsencroft Journal of Organic Chemistry, 2001 , vol. 66, # 7 p. 2414 - 2421

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Citation Number: 69

Abstract

Ammonium ylides derived from the Cu (II)-catalyzed decomposition of α-diazo carbonyls tethered to tertiary amines underwent a benzylic Stevens [1, 2]-rearrangement to give tetrahydroisoquinolines or benzazepines containing fused five-membered rings, a feature found in the cephalotaxus alkaloids. Model studies were also carried out toward the synthesis of lennoxamine, a member of the isoindolobenzazepine family of alkaloids. The ...