Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids

Li, J.; Li, F.; King-Smith, E.; Renata, H.; Li, J; Li, F; King-Smith, E; Renata, H

doi:10.1038/s41557-019-0407-6

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Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids

Li, J.; Li, F.; King-Smith, E.; Renata, H.

Nature Chemistry 12(2): 173-179

2020

ISSN/ISBN: 1755-4349

PMID: 31959962

DOI: 10.1038/s41557-019-0407-6
Accession: 072116114

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Summary

Meroterpenoids are natural products of hybrid biosynthetic origins-derived from both terpenoid and polyketide pathways-with a wealth of biological activities. Given their therapeutic potential, a general strategy to access these natural products in a concise and divergent fashion is highly desirable. Here, we report a modular synthesis of a suite of oxidized meroterpenoids using a hybrid synthetic strategy that is designed to harness the power of both biocatalytic and radical-based retrosynthetic logic. This strategy enables direct introduction of key hydroxyl groups and rapid construction of key bonds and stereocentres, facilitating the development of a concise route (7-12 steps from commercial materials) to eight oxidized meroterpenoids from two common molecular scaffolds. This work lays the foundation for rapid access to a wide range of oxidized meroterpenoids through the use of similar hybrid strategy that combines two synthetic approaches.