Ortho-acylation Method for Synthesis of Xanthones and Sparstolonin B (SsnB) Derivatives


Reference #: 00989

Invention Description:

The subject invention is a novel one-step, high yielding ortho-acylation reaction of phenols capable of synthesizing xanthones under considerably mild conditions.


Xanthones are important structural units in organic chemistry and widely present in natural products. Their derivatives show diverse physicochemical and pharmacological properties including antioxidant, anti-inflammatory, antibacterial, antineoplastic, and vasodilator. Furthermore, xanthones are important intermediates for synthesizing Sparstolonin B (SsnB), an effective anti-inflammatory compound derived from the Sparganium stoloniferum herb which is traditionally used in Chinese medicine. Yet most syntheses require advanced starting materials, multi-step transformations, or exotic reaction conditions, e.g. Friedel-Crafts reactions.

Advantages and Benefits:

  1. While most methods for synthesizing xanthones involve multistep transformations, the subject invention is a one-step synthesis that also produces high yields.

  2. It offers an alternative to the widely used Lewis acid-catalyzed Friedel-Crafts acylation reaction which often suffers from the harsh reaction conditions, usage of air/water sensitive Lewis acid, and incompatibility with many functional groups.

  3. The high-yield of this ortho-acylation method makes it easy to synthesize SsnB and its derivatives through a subsequent sequence of reactions.

Potential Applications:

Synthesis of xanthone derivatives

Patent Information:
Title App Type Country Serial No. Patent No. File Date Issued Date Expire Date Patent Status
New Methodology for the Synthesis of Xanthones Utility United States 14/049,809 9,163,002 10/9/2013 10/20/2015    
For Information, Contact:
Technology Commercialization
University of South Carolina
Qian Wang
Jim Hu
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