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Sequential Five-Component Synthesis of Spiropyrrolidinochromanones

2009; American Chemical Society; Volume: 74; Issue: 17 Linguagem: Inglês

10.1021/jo900992w

1520-6904

Stefano Marcaccini, Ana G. Neo, Carlos F. Marcos,

Oxidative Organic Chemistry Reactions

Herein we report a novel, diastereoselective, one-pot, two-step, sequential synthesis of highly functionalized natural product-like spiropyrrolidinochromanones. The process consists of an Ugi four-component condensation of 3-formylchromones with amines, isocyanides, and glyoxylic acids followed by a nucleophilic conjugate addition and intramolecular cyclization. The experimental simplicity and tolerance to a wide variety of substituents makes this method suitable for combinatorial synthesis.