Orthogonal Syntheses of γ-Carbolinone and Spiro[pyrrolidinone-3,3′]indole Derivatives in One Pot through Reaction Telescoping

• DOI: 10.1021/acs.joc.1c00141
• Publication Date: 2021-03-15T18:30:46Z
• Authors: Souvik Guha; Satyanarayana Gadde; Naresh Kumar; David StClair Black; Subhabrata Sen
• Keywords: Reaction conditions; Sequence (biology); Telescoping series

Herein we report a series of telescoping methodologies for one pot synthesis biologically relevant γ-carboline derivatives 6 and spiro[pyrrolidinone-3,3′]indole 7. Initially the three consecutive steps cyclopropanation, phthalimide deprotection, Boc-deprotection have been congregated in single reaction vessel to afford ∼1:1 mixture Next, careful optimization sequence conditions generated an orthogonal approach access compounds 7 exclusively. Air oxidation γ-carbolinones afforded aromatic γ-carbolines 8.