Modular Divergent Synthesis of Indole Alkaloid Derivatives by an Atypical Ugi Multicomponent Reaction

Abstract: We present an Ugi multicomponent approach to explore the chemical space around Aspidosperma‐type monoterpene indole alkaloids. By variation of the isocyanide and carboxylic acid inputs we demonstrate the rapid generation of molecular diversity and the possibility to introduce handles for further modification. The key Ugi three‐component reaction showed full diastereoselectivity towards the cis‐fused ring system, which can be rationalized by DFT calculations that moreover indicate that the reaction proceeds via a Passerini‐type hydrogen bonding mechanism. Several post‐Ugi modifications were also performed, including Pictet‐Spengler cyclization to highly complex nonacyclic natural product hybrid scaffolds.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Modular Divergent Synthesis of Indole Alkaloid Derivatives by an Atypical Ugi Multicomponent Reaction ; day:10 ; month:04 ; year:2024 ; extent:6 ; Chemistry - a European journal ; (10.04.2024) (gesamt 6)

Contributors, Places and Time

• Creator: Horst, Brendan ; van Duijnen, Niels ; Janssen, Elwin ; Hansen, Thomas ; Ruijter, Eelco

Further information

• DOI: 10.1002/chem.202400477
• URN: urn:nbn:de:101:1-2024041114311849093553
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 01.08.2025, 5:29 PM CEST