4.7 Article

Sequential Five-Component Synthesis of Spiropyrrolidinochromanones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 17, Pages 6888-6890

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo900992w

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Funding

  1. Instituto de Salud Carlos III [PI081234]
  2. Junta de Extremadura
  3. FEDER [PRI07A032, PRI08A039]

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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.

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