A Proposal for a Regio- , Stereo- , and Enantioselective Synthesis of Menthol

In this brief report , a new synthesis route for L-(-)-menthol is proposed and elaborated . While menthol is a relatively simple molecule , the total synthesis of the levo enantiomer from common starting materials is a surprisingly difficult task . The combination of simplicity of structure yet challenging synthesis route will make this study of particular interest to undergraduate organic chemistry students .

The regio- and stereochemistry of the intermediates and product are controlled by a judicious selection of the component synthons , and of skeletal formation and modification by various reagents . Enantioselectivity may be at least partially controlled by the use of a known catalyst prepared with optically-active ligands coordinated to an electrophilic cation .

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I highly recommend the following two web pages , which contain a wealth of information about menthol :

Simon Cotton , "Menthol" , Molecule of the Month website (University of Bristol , UK) , August 2007 , http://www.chm.bris.ac.uk/motm/menthol/mentholh.htm ; and ,

Leffingwell & Associates , "Menthol - A Cool Place" , http://www.leffingwell.com/menthol1/menthol1.htm .