Chiral Cyclodimerization Reactions: Construction of Nonnatural Dimeric Carbazoles from (±)-4-Methylene-3-hydroxytetrahydrocarbazoles

Abstract

AbstractIn this Synpacts article, we describe the concept of cyclodimerization in the biosynthesis and biomimetic synthesis of natural products and unnatural products. We also discuss key details of our discovery and development of a biomimetic-like, selective, homo- and heterochiral cyclodimerization strategy for the construction of nonnatural dimeric carbazole frameworks by employing a formal [3+2] annulation. Our work also demonstrated a novel reactivity of 1-(indol-2-yl)pent-4-yn-3-ols, and their potential as new synthetic building blocks in organic synthesis.1 Introduction: Chiral Cyclodimerization Reactions2 Biomimetic Syntheses of Natural Products through Chiral Cyclodimerizations3 Bioinspired Synthesis of Nonnatural Dimeric Carbazoles through Selective Chiral Cyclodimerizations4 Future Perspectives and Conclusions