Efforts towards the formal synthesis of bakuchiol via small molecule manipulation

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Anderson Timothy Stacy IV (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/
Kimberly Petersen

Abstract: Bakuchiol is a monoterpinoid compound found mainly in the seeds of Psoralea coryfolia Linn, which is indigenous to Southeast Asia. Since its discovery and isolation in 1967, it has been reported to contain a multitude of health benefits. It exhibits antitumor, antidiabetic, antimicrobial and recently discovered anti-aging properties. There are multiple ways in which bakuchiol has been synthesized. Research herein used the lactonization of an achiral hydroxydiester as the key step in a series of small molecule manipulations which formed compounds for the future synthesis of bakuchiol. The goal described in this thesis was to create a new synthetic pathway for bakuchiol. The steps included two lactonizations, two ring openings, two protections and subsequent deprotections of alcohol groups, a Horner-Wadsworth-Emmons, and a Grignard reaction. These steps built upon the all carbon quaternary center, which can be installed using the desymmetrization method developed by the Petersen lab, and were used to manipulate the molecule to form the desired bakuchiol precursors. Herein is presented the efforts and methodology developed towards the total synthesis of bakuchiol via small molecule manipulation upon a quaternary center. This pathway may also be of use for the development of various analogs of bakuchiol which may have various medicinal properties.

Additional Information

Language: English
Date: 2014
Bakuchiol, Psoralea coryfolia Linn seeds,
Psoralea $x Molecular aspects

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