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Lessons learned from macrolide synthesis.

Johann Mulzer¹, Harry J Martin

¹Institut für Organische Chemie der Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria. Johann.Mulzer@univie.ac.at

Chemical Record (New York, N.Y.)

|February 6, 2004

Summary

Researchers achieved stereocontrolled synthesis of epothilone B using an early epoxide strategy. They also advanced laulimalide synthesis with ene-macrocyclization and Sharpless kinetic resolution, and completed tartrolon B synthesis via aldol addition.

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Area of Science:

Organic Chemistry
Natural Product Synthesis

Background:

Macrolides are complex natural products with significant biological activity.
Efficient and stereocontrolled synthesis of macrolides remains a challenge in organic chemistry.

Purpose of the Study:

To describe recent advances in the laboratory concerning the synthesis of three complex macrolides: epothilone B, laulimalide, and tartrolon B.
To highlight novel synthetic strategies and methodologies developed during these syntheses.

Main Methods:

Epothilone B: Development of the "early epoxide approach" for stereocontrolled synthesis.
Laulimalide: Application of auxiliary-controlled ene-macrocyclization and Sharpless kinetic resolution for regioselective epoxidation.
Tartrolon B: Utilization of substrate-controlled aldol addition to construct the carbon skeleton.

Main Results:

Achieved the first completely stereocontrolled synthesis of epothilone B.
Successfully employed kinetic resolution for regioselective epoxidation in laulimalide synthesis.
Completed the synthesis of tartrolon B, assembling its entire carbon skeleton.

Conclusions:

The developed synthetic strategies offer powerful tools for the construction of complex macrolide natural products.
These syntheses demonstrate significant progress in stereocontrol and efficiency in natural product synthesis.

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