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

Abstract

In 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 Reactions

2 Biomimetic Syntheses of Natural Products through Chiral Cyclodimerizations

3 Bioinspired Synthesis of Nonnatural Dimeric Carbazoles through Selective Chiral Cyclodimerizations

4 Future Perspectives and Conclusions

Key words

biomimetic synthesis - cyclodimerizations - carbazole dimers - indolylpentynols

Publication History

Received: 21 September 2023

Accepted after revision: 16 October 2023

Accepted Manuscript online:
16 October 2023

Article published online:
27 November 2023

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