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Related Experiment Video

Updated: Jan 16, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Stereoselective Syntheses of Cyclic Microsclerodermin Derivatives.

Kevin Bauer¹, Uli Kazmaier^1,2

¹Organic Chemistry, Saarland University, Campus C4.2, 66123, Saarbrücken, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|September 27, 2025

Summary

Researchers synthesized six cyclic microscleroderma derivatives from l-xylose and d-arabinose. Key methods included stereoselective Sakurai allylations and photochemical Wolff rearrangements, followed by cross-metathesis for aromatic side chain introduction.

Keywords:

Arndt‐Eistert homologation cyclic peptides microsclerodermins sakurai reaction tetrahydrofurans

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Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Medicinal Chemistry

Background:

Cyclic microscleroderma derivatives are complex molecules with potential therapeutic applications.
Efficient synthetic routes are needed to access novel analogs for further study.

Purpose of the Study:

To develop a novel synthetic strategy for producing diverse cyclic microscleroderma derivatives.
To explore the utility of specific reactions in constructing these complex scaffolds.

Main Methods:

Synthesis initiated from readily available carbohydrates: l-xylose and d-arabinose.
Key transformations involved stereoselective Sakurai allylations, influenced by Lewis acid choice.
Photochemical Wolff rearrangements were employed using complex aminofuranosides.
Aromatic side chains were appended through cross-metathesis.

Main Results:

Successfully synthesized six distinct cyclic microscleroderma derivatives.
Demonstrated control over stereochemistry during the Sakurai allylation step.
Confirmed the successful introduction of aromatic moieties via cross-metathesis.

Conclusions:

The developed synthetic route provides access to a library of cyclic microscleroderma derivatives.
The study highlights the versatility of Sakurai allylation and photochemical Wolff rearrangement in carbohydrate chemistry.
This methodology can be applied to generate analogs for structure-activity relationship studies.