Asymmetric Alkene and Arene Halofunctionalization Reactions in Meroterpenoid Biosynthesis

Dedicated to Professor William Fenical for his discovery of halogenated marine bacterial meroterpenoids

Published as part of the Cluster Alkene Halofunctionalization

Abstract

Meroterpenoid natural products are important bioactive molecules with broad distribution throughout nature. In Streptomyces bacteria, naphthoquinone-based meroterpenoids comprise a simple yet structurally fascinating group of natural product antibiotics that are enzymatically constructed through a series of asymmetric alkene and arene halofunctionalization reactions. This account article highlights our discovery and characterization of a group of vanadium-dependent chloroperoxidase enzymes that catalyze halogen-assisted cyclization and rearrangement reactions and have inspired biomimetic syntheses of numerous meroterpenoid natural products.

1 Introduction

2 Early Biosynthetic Insights and the Characterization of Alkene Halofunctionalization in Napyradiomycin Biosynthesis

3 Discovery of the Merochlorin Natural Products and Enzymatic Aryl Halofunctionalization

4 Discovery and Development of Unifying THN-Based Meroterpenoid Biosynthesis and Synthesis Approaches

5 Insights into Naphterpin and Marinone Biosynthesis Involving Cryptic Aryl Halofunctionalization Reactions

6 Closing Thoughts

Key words

biomimetic - haloperoxidase - α-hydroxyketone rearrangement - meroterpenoid - natural product biosynthesis

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