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

Description:

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.

Background:

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
technology@sc.edu
Inventors:
Qian Wang
Jim Hu
Keywords:
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