Novel Method to Prepare Isoflavene and Chromane Analogs

Description:

Project ID: D2011-60

Novelty: A practical and novel intramolecular wittig reaction procedure for the production of variously substituted isoflavene and chromane analogs.

Value proposition: Development of safe and economic manufacturing processes for natural product derivatives have always been a priority in the industry. Isoflavene systems require thallium mediated rearrangement step which is highly toxic to both the humans and to the environment. The researchers at The University of Toledo have developed a novel synthetic route, an intramolecular wittig reaction, to synthesize higher yields of isoflavone and chromane analogs. This method does not require thallium and the yields form this wittig process are much more consistent and higher than for the thallium – mediated process making it more conducive to devising manufacturing scale process that can have reduced costs. 

Invention description: Researchers at The University of Toledo have developed a chemical process for preparing isoflavene and chromane compounds by using an intramolecular wittig reaction. This method provides a more economic and safe method to synthesize the natural product derivatives. Researchers have shown the applicability of this process in synthesis of phenoxodiol and its chromane analog, racemic vestitol, bolusanthhin III, glycinol, glyceollin I & II, and triphentriol. The end products so fromed using this method have shown properties indicative for use as cancer prevention and treatment agents. Thus, this invention provides practical and improved method for synthesizing isoflavene and chromane analogs and intermediates in higher yields that display useful pharmacological properties similar to the naturally-derived materials.

IP status: U.S. Utility Patent #8,507,549

References:

1.   Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I

2.  Total Syntheses of Racemic and Natural Glycinol

Patent Information:
Category(s):
Chemistry
Pharmaceuticals
For Information, Contact:
Stephen Snider
AVP Tech Transfer
The University of Toledo
419 530 6225
Stephen.Snider@utoledo.edu
Inventors:
Paul Erhardt
Rahul Khupse
Amarjit Luniwal
Keywords:
Chromane
Glycenol
Glyceollin
Isoflavin
Soy