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Synthesis of a Water-soluble Metal–Organic Complex Array

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Published on: October 8, 2016

Total Synthesis of (±)-Berkeleyone A.

Masha Elkin¹, Suzanne M Szewczyk¹, Anthony C Scruse¹

¹Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Journal of the American Chemical Society

|January 20, 2017

Summary

This study reports a 13-step total synthesis of the fungal meroterpenoid berkeleyone A, utilizing novel cyclization and isomerization reactions to construct its complex molecular skeleton.

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Area of Science:

Organic Chemistry
Natural Product Synthesis
Fungal Metabolomics

Background:

Meroterpenoids are complex fungal metabolites with diverse biological activities.
Berkeleyone A is a fungal meroterpenoid whose total synthesis presents a significant chemical challenge.
Understanding the biosynthesis of meroterpenoids can provide insights into fungal metabolic pathways.

Purpose of the Study:

To achieve the first total synthesis of the fungal meroterpenoid berkeleyone A.
To develop novel synthetic methodologies for constructing complex polycyclic frameworks.
To provide access to berkeleyone A and related natural products for further biological and biosynthetic studies.

Main Methods:

A 13-step total synthesis strategy was designed and executed.
Key reactions included an epoxide-initiated, β-ketoester-terminated polycyclization.
An isomerization-cyclization cascade was employed to form the bicyclo[3.3.1]nonane core.

Main Results:

The total synthesis of berkeleyone A was successfully accomplished in 13 steps.
Two novel cascade reactions were developed and demonstrated.
A 6-step synthesis of the carbocyclic core enabled access to protoaustinoid A and berkeleyone A.

Conclusions:

The reported synthesis provides a viable route to berkeleyone A and related natural products.
The developed synthetic methods are applicable to the construction of other complex polycyclic molecules.
This work facilitates future investigations into the biosynthesis of fungal meroterpenoids.