The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids

R. Suau, R. Rico, F. Nájera, F. J. Ortiz-López, J. M. López-Romero, M. Moreno-Mañas, A. Roglans

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)

Abstract

We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported. © 2004 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5725-5735
JournalTetrahedron
Volume60
Issue number27
DOIs
Publication statusPublished - 28 Jun 2004

Keywords

  • 4,5-Dioxoaporphine
  • 4-Hydroxy-dehydroaporphine
  • Apomorphine
  • Aporphine
  • Aporphinoids
  • Cascade cyclization
  • Oxalyl chloride
  • Palladium
  • Reduction
  • Suzuki cross-coupling

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