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Preparation and Reactions of Sulfides

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Related Experiment Video

Updated: Jun 10, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Published on: March 6, 2019

Practical Synthesis of Macrobicyclic Thiolincosamines.

Kelvin J Y Wu¹, Ben I C Tresco¹, Junzhe Xiao¹

¹Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society

|October 12, 2024

Summary

Scalable syntheses of thiolincosamine fragments for antibiotic candidates BT-33 and cresomycin were achieved. A key step involved a diastereoselective allenylzinc addition to a sulfinimine intermediate, enabling efficient fragment construction.

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Published on: April 9, 2018

Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

Antibiotic resistance necessitates the development of novel therapeutic agents.
Thiolincosamine fragments are crucial components of complex, biologically active molecules.
Efficient synthetic routes are required for antibiotic candidates like BT-33 and cresomycin.

Purpose of the Study:

To present scalable synthetic strategies for the northern macrobicyclic thiolincosamine fragments.
To detail a key diastereoselective transformation for constructing these complex fragments.
To enable the synthesis of antibiotic candidates BT-33 and cresomycin.

Main Methods:

Development of scalable synthetic routes.
Utilizing a zinc-promoted Barbier-type propargylation protocol.
Employing a highly diastereoselective addition of an allenylzinc nucleophile to an Ellman sulfinimine intermediate.

Main Results:

Successful scalable syntheses of thiolincosamine fragments were achieved.
The key transformation demonstrated high diastereoselectivity.
The protocol proceeded with dynamic kinetic resolution.
Efficient synthesis utilized only 1.2 equiv of propargyl bromide precursors.

Conclusions:

The presented synthetic methods provide scalable access to key fragments of complex antibiotics.
The developed Barbier-type propargylation protocol is effective for diastereoselective synthesis.
This work facilitates further development of antibiotic candidates BT-33 and cresomycin.