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Related Experiment Video

Updated: May 15, 2025

CRISPR/Cas9 Editing of the C. elegans rbm-3.2 Gene using the dpy-10 Co-CRISPR Screening Marker and Assembled Ribonucleoprotein Complexes.

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Published on: December 11, 2020

Advancing Total Synthesis Through Skeletal Editing.

Reem Al-Ahmad¹, Mingji Dai¹

¹Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.

Accounts of Chemical Research

|April 10, 2025

Summary

This summary is machine-generated.

Skeletal editing offers a novel approach to total synthesis, enabling efficient construction of complex molecules by rearranging carbon frameworks. This strategy streamlines natural product synthesis through a build-edit-decorate workflow, enhancing chemical innovation.

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Area of Science:

Organic Chemistry
Total Synthesis
Medicinal Chemistry

Background:

Total synthesis advances chemical strategies by replicating and surpassing natural complexity.
Skeletal editing, a newer approach, reconfigures molecular frameworks through atom insertion, deletion, exchange, and rearrangement.
This method harnesses potential energy and reactivity for novel electronic and spatial configurations.

Purpose of the Study:

To detail a program utilizing skeletal editing-based retrosynthetic logic for natural product synthesis.
To showcase the development and application of new skeletal editing methods.
To demonstrate the strategy's potential in medicinal chemistry and materials science.

Main Methods:

Employed one-carbon insertion editing (Ciamician-Dennstedt rearrangement, Büchner-Curtius-Schlotterbeck ring expansion) for Lycopodium alkaloids.
Utilized cyclobutane strain for cut-and-insert editing and C-C bond migratory ring expansion in diterpene synthesis.
Applied a build-edit-decorate workflow for assembling and modifying molecular scaffolds.

Main Results:

Successfully streamlined the total syntheses of complanadine and phleghenrine.
Achieved synthesis of crinipellin and gibberellin diterpenes by editing cyclobutane precursors.
Synthesized seven monoterpene indole alkaloids, demonstrating divergent skeletal editing potential.

Conclusions:

Skeletal editing provides a powerful and efficient strategy for complex molecule synthesis.
The build-edit-decorate workflow mirrors biosynthesis, enabling rapid complexity building with step economy.
This approach offers a new retrosynthetic logic for overcoming synthetic bottlenecks in natural product synthesis.