The Journal of organic chemistry

Tandem Intramolecular Photocycloaddition− Retro-Mannich Fragmentation as a Route to Spiro [pyrrolidine-3, 3′-oxindoles]. Total Synthesis of (±)-Coerulescine,(±)- …

JD White, Y Li, DC Ihle

Index: White, James D.; Li, Yang; Ihle, David C. Journal of Organic Chemistry, 2010 , vol. 75, # 11 p. 3569 - 3577

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Citation Number: 47

Abstract

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2+ 2] cycloaddition to the indole 2, 3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro [indoline-3, 3′-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient cyclobutane. The tandem intramolecular photocycloaddition− ...