Synthesis of Complex Tetracyclic Fused Scaffolds Enabled by (3 + 2) Cycloaddition

Vincent Porte, Branca C. van Veen, Haoqi Zhang, Paolo Piacentini, Sergio Armentia Matheu, Sophie Woolford, Kevin R. Sokol, Saad Shaaban, Harald Weinstabl, Nuno Maulide (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

We describe the single-step formation of complex tetracyclic fused scaffolds enabled by (3 + 2) cycloaddition of azomethine ylides. Various indoles, N-protecting groups, and amino acids are well tolerated. The products are obtained in a catalyst-free manner with moderate to excellent yield and high diastereoselectivity. Representing a new scaffold that is not yet found in nature, the construction of pyrrolidine-fused cyclohepta-, azepino-, or oxepinoindoles could be found valuable in the synthesis of new pseudo-natural products.

Original languageEnglish
Pages (from-to)4873-4876
Number of pages4
JournalOrganic Letters
Volume26
Issue number23
Early online date2024
DOIs
Publication statusPublished - 14 Jun 2024

Austrian Fields of Science 2012

  • 104015 Organic chemistry
  • 301207 Pharmaceutical chemistry

Cite this