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Published on: July 28, 2022

Total synthesis of biselide A.

Venugopal Rao Challa¹, Daniel Kwon¹, Matthew Taron¹

¹Department of Chemistry, Simon Fraser University Burnaby British Columbia V5A 1S6 Canada rbritton@sfu.ca.

Chemical Science

|June 25, 2021

Summary

Scientists achieved a total synthesis of marine macrolide biselide A using a chiral building block. This research offers insights into biselide A

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Area of Science:

Organic Chemistry
Marine Natural Products
Medicinal Chemistry

Background:

Marine macrolides like biselide A are complex natural products with potential therapeutic applications.
Developing efficient synthetic routes is crucial for accessing these compounds for further study.

Purpose of the Study:

To describe a total synthesis of the marine macrolide biselide A.
To investigate the mechanism of action of biselide A in biological systems.

Main Methods:

Enantioselective synthesis utilizing an enantiomerically enriched α-chloroaldehyde.
Macrocycle construction via a macrocyclic Reformatsky reaction.
Biological assays to assess effects on cell division and microtubule organization.

Main Results:

Successful total synthesis of biselide A in a longest linear sequence of 18 steps.
Identification of biselide A's mechanism of action involving disruption of cell division.
Demonstrated impact on microtubule cytoskeleton organization.

Conclusions:

A concise and efficient synthetic route to biselide A has been established.
Biselide A's anticancer potential is linked to its effects on microtubule dynamics.
This work provides a foundation for medicinal chemistry efforts on related anticancer marine macrolides.