An Asymmetric One-Pot Synthesis of the (+) and (-) Enantiomers of an Estrogenic Carboxylic Acid
Project Leader: Yuqing Hou
Unit: College of Science, Dept. of Chemistry and Biochemistry; College of Agricultural Sciences, Dept. of Animal Science, Food and Nutrition
Brief Description:
This disclosure relates to a commercially viable, one-pot, asymmetric synthesis of the (+) and (-) enantiomers of a highly estrogenic carboxylic acid.
Patent Status:
Patent application in process.
Potential Commercial Uses:
These enantiomers have a number of potential therapeutic applications, such as estrogen replacement, treatment of prostate cancer and breast cancer, prevention of osteoporosis, ameliorating male-pattern baldness, etc. The (+) and (-) enantiomers of this acid have different biological activities. Previously, a multiple-step process was required and it produced the racemic acid; the pure (+) and (-) enantiomers were then obtained only by an expensive resolution process which reduced the yield of each enantiomer while raising the cost of production. In contrast, our one-pot asymmetric synthetic process not only produces the target carboxylic acid in good yield from commercially available starting materials, without the need to separate intermediates, but directly and selectively enriches one enantiomer over the other and can even produce the desired enantiomer exclusively.
Contact:
Jeff Myers, Senior Technology Transfer Specialist, (618) 453-4543, fax: (618) 453-8038