Catalyst‐Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones

Abstract

Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.

Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds

“…The follow-up studies from the same group 50 identified that utilizing chiral bisphosphine (R)-xylylBINAP or (S)-DTBM-SEGPHOS as the ligand could realize the highly enantioselective version of these two reactions. 51 Cu-catalyzed asymmetric propargylic substitution reaction has seen significant progress in recent years. 52 However, the scope of the carbon nucleophiles compatible with this reaction is still limited.…”

Structurally Divergent Lithium Catalyzed Friedel–Crafts Reactions on Oxetan‐3‐ols: Synthesis of 3,3‐Diaryloxetanes and 2,3‐Dihydrobenzofurans

“…This presents ar are example of ad ivergentr eaction whereby ar egiochemical difference leads to structurallyd istinct products, so avoidingc losely relatedi somers. [17]…”

Scaffold Diversity Synthesis Delivers Complex, Structurally, and Functionally Distinct Tetracyclic Benzopyrones

“…Incorporating structural diversity, [19] including ring diversity to any compound class is aimed to enhancei ts potentialf or functional diversity,t hat is, to provide diversely bioactive molecules that can be used as tools to pursue chemical biology or drug-discovery goals. [11] To determine the potential of these significantly complex and diverse tetracyclic benzopyrones,t he collection was evaluated in two different cell-based screenings (Figure 2).…”

“…[24] In parallel, the compound collection was screenedi nh uman cervical cancerH eLa cells at ac oncentration of 30 mm to determine their cytotoxicity,i nfluence on cytoskeleton, and mitosis. [6b] Among four benzopyrones ubclasses (10,12,(15)(16)19), only 16 a-d weref ound to be cytotoxic (Table S1 and Figure S6). Regioisomeric analogues 15 did not display any influence on HeLa cells.…”