Nonappa, * and Maitra, Uday (2007) First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α-Hydroxycholic Acid. In: European Journal of Organic Chemistry, 2007 (20). pp. 3331-3336.
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The first chemical synthesis of pythocholic acid, a major component of python’s bile, and $3\alpha$,$7\alpha$,$12\alpha$,$16\alpha$-tetrahydroxy-$5\beta$-cholan-24-oic acid ($16\alpha$-hydroxycholic acid), a minor component in Shoebill stork’s bile, was achieved starting from readily available cholic acid in overall yields of 5% and 5.5%, respectively, through a common intermediate. A biomimetic template-directed remote functionalization strategy was utilized to selectively functionalize C-16 of the steroid skeleton. This synthesis involves a series of regio and chemoselective transformations. Pythocholic acid showed unusually low critical micellar concentration (CMC) with high cholesterol solubilization ability.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to John Wiley & Sons, Inc.|
|Keywords:||Pythocholic acid;Oxidation;Critical micellar concentration;Regio and chemoselective;Remote functionalization|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||10 Jun 2008|
|Last Modified:||19 Sep 2010 04:45|
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