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Concise Synthesis of Broussonone A.

Hyeju Jo¹, Minho Choi², Mayavan Viji³

¹College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, Korea. hjjo317@chungbuk.ac.kr.

Molecules (Basel, Switzerland)

|September 15, 2015

Summary

Researchers developed a fast total synthesis for broussonone A, a natural p-quinol compound. This method utilizes Grubbs II catalyst cross-metathesis and selective oxidative dearomatization, overcoming challenges with specific aromatic substrates.

Keywords:

Grubbs catalyst PIFA broussonone A cross metathesis oxidative dearomatization total synthesis

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Area of Science:

Organic Chemistry
Natural Product Synthesis

Background:

Broussonone A is a p-quinol natural product.
Total synthesis of complex natural products presents significant challenges.

Purpose of the Study:

To develop a concise and efficient total synthesis of broussonone A.
To optimize challenging cross-metathesis reactions involving ortho-alkoxystyrenes.

Main Methods:

Utilized Grubbs II catalyst for cross-metathesis of aromatic subunits.
Employed chemoselective oxidative dearomatization in the presence of phenol groups.
Investigated and optimized the cross-metathesis of ortho-alkoxystyrenes.

Main Results:

Achieved a concise and expeditious total synthesis of broussonone A.
Successfully overcame catalyst inhibition issues in ruthenium-catalyzed metathesis of ortho-alkoxystyrenes.
Demonstrated the effectiveness of the developed synthetic strategy.

Conclusions:

The developed synthetic approach provides an efficient route to broussonone A.
The optimization of the cross-metathesis reaction expands the utility of ruthenium-catalyzed metathesis for challenging substrates.
This work contributes to the field of natural product synthesis and methodology development.