Synthetic Approaches toward the Batzelladine Class of Guanidinium Alkaloids

Abstract

Polycyclic guanidinium alkaloids (PGAs) are a class of nitrogen-containing marine natural products characterized by a vessel unit, a linker, and an anchor unit. Batzelladines, a specific subclass of PGAs, exhibit diverse biological activities and structural complexities. This short review discusses various synthetic methods developed to access batzelladine natural products, highlighting the key disconnections utilized in each synthetic strategy.

1 Introduction

2 Polycyclic Guanidinium Alkaloids

3 Batzelladine Natural Products

4 Strategies in Batzelladine Synthesis

4.1 Aza-Michael Addition

4.2 Biginelli Condensation

4.3 1,3-Dipolar Cycloaddition

4.4 [4+2] Annulation of N-Alkyl Imines and Vinyl Carbodiimides

4.5 Free-Radical Cyclization

4.6 Palladium-Catalyzed Carboamination

4.7 Rhodium-Catalyzed [4+3] Cycloaddition

4.8 A Bicyclic β-Lactam Intermediate

5 Non-Total Synthesis Contributions

6 Conclusion

Key words

batzelladine - guanidinium - alkaloids - natural products - marine sponges

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