Access to Polycyclic Alkaloid‐Like Structures by Coupling the Passerini and Ugi Reactions with Two Sequential Metal‐Catalyzed Cyclizations. Issue 18 (25th August 2016)

• Record Type: Journal Article
• Authors: Spallarossa, Martina; Banfi, Luca; Basso, Andrea; Moni, Lisa; Riva, Renata
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 18(2016)
• Page Start: 2940
• Page End: 2948
• Publication Date: 2016-08-25
• Subjects: allylic compounds -- molecular diversity -- multicomponent reactions -- nucleophilic substitution -- ring-closing metathesis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600638
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Complex polycyclic compounds resembling some natural alkaloids have been prepared in only three high yielding steps by combining the Ugi or Passerini multicomponent reactions with two metal‐catalyzed cyclizations: an intramolecular Tsuji–Trost reaction of the isocyanide‐derived amide followed by a ring‐closing metathesis. Scaffold diversity may be explored by the appropriate choice of starting unsaturated isocyanides. The Tsuji–Trost cyclization proceeds with moderate to good diastereoselectivity, and the major diastereomer was in most cases isolated in the pure form. Abstract :