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Updated: Dec 30, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Programmable meroterpene synthesis.

Xingyu Shen¹, Chi P Ting¹, Gong Xu¹

¹Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94702, USA.

Nature Communications

|January 26, 2020

Summary

This summary is machine-generated.

Researchers developed a 10-step synthesis for bicyclo[3.3.1]nonane natural products, including garsubellin A. This strategy enables programmable synthesis of diverse meroterpene chemotypes for potential therapeutic applications.

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Last Updated: Dec 30, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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Published on: October 4, 2019

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Area of Science:

Organic Chemistry
Natural Product Synthesis
Medicinal Chemistry

Background:

The bicyclo[3.3.1]nonane core is prevalent in over 1000 natural products, exhibiting bioactivity against neurodegenerative diseases, infections, and cancer.
Meroterpenes, natural products of mixed polyketide/terpenoid origin, are a significant source of bicyclo[3.3.1]nonane-containing compounds.

Purpose of the Study:

To establish a general synthetic strategy for accessing bicyclo[3.3.1]nonane-containing natural products.
To achieve the total synthesis of garsubellin A, a known enhancer of choline acetyltransferase.

Main Methods:

Development of an abiotic annulation/rearrangement strategy.
A 10-step total synthesis of garsubellin A was executed.
Demonstration of a programmable assembly process for diverse meroterpene chemotypes.

Main Results:

Successful 10-step total synthesis of garsubellin A.
Validation of a versatile synthetic strategy for bicyclo[3.3.1]nonane derivatives.
The strategy allows for the creation of multiple, diverse meroterpene chemotypes.

Conclusions:

The developed synthetic strategy provides efficient access to the bicyclo[3.3.1]nonane scaffold.
This approach facilitates the synthesis of biologically relevant meroterpenes.
The programmable assembly offers a pathway to novel therapeutic agents.