|Title:||Professor, Organic Chemistry|
B.S., magna cum laude, 1966, Loyola University
Ph.D., 1971, Northwestern University
My research interests at the present time cover three general areas: (a) total synthesis of carotenoids and retinoids; (b) development of novel synthetic methodology useful in the preparation of flavor and fragrance materials; and (c) new methods for construction of various carbocyclic ring systems.
In the area of total synthesis, most of our recent efforts have been directed toward developing novel routes to vitamin A (1) and analogues (known as retinoids), as well as to alpha-tocopherol (vitamin E). Recent accomplishments in this area include the synthesis of novel phosphonate reagents which have subsequently been shown to be useful in the stereoselective synthesis of retin-A (all trans-retinoic acid), accutane (an anti-acne drug), lycopene, and beta-carotene (2). The latter compound is an important additive in oleomargarine and certain skin creams, a yellow coloring agent for certain foods, and has been shown by recent studies at the National Cancer Institute to have potent inhibitory properties towards several common types of cancer.
In the area of flavor and fragrance materials, we have recently developed a novel route to citral starting with isoprene. Citral is a specialty chemical used in the flavor and fragrance ("lemon scent") industries, as well as in the manufacture of vitamins A and E and several widely-used carotenoids, including beta-carotene. We have also developed novel methodologies for effecting crossed aldol condensations between two different enolizable aldehydes and vinylogous aldol reactions.
Among the novel cyclization methodologies we are developing are: (a) a facile route to cyclopropanones; (b) a ring-expansion methodology for the synthesis of tropones and tropolones (an important class of nonbenzenoid aromatic compounds); and (c) conjugate addition-induced ring closure reactions. Our work in this latter area will lead to construction of a variety of carbocyclic ring systems, including fused, spiro and bridged bicyclic systems, that serve as structural units for a myriad of terpenoid natural products.
J.H. Babler and N.A. White, "A Convenient Methodology for the Chemoselective Reduction of a Wide Variety of Functionalized Alkenes" Tetrahedron Lett., 2010, 51, 439.
J.H. Babler, "Methods for Preparing Aldehydes by Self-Aldol Condensation" U.S. Patent 7,632,973 B2 (December 15 2009).
J.H. Babler, M.C. Atwood, J.E. Freaney, and A.R. Viszlay, "The Role of Imine-Enamine Tautomerism in Effecting Cross-Aldol Condensations" Tetrahedron Lett., 2007, 48, 7665.
J.H. Babler, B.D. Steinkamp, and M.C. Atwood, "A Regioselective Retroalkynylation Process: Part of an Efficient Route for the Converson of beta-Ionone to Canthaxanthin and Other Oxygenated Carotenoids" Synth. Commun., 2002, 32, 329.
J.H. Babler and H.W. Posvic, "C-15 Phosphonate Reagent Compositions for the Manufacture of Compounds Such as Lycopene and Methods of Synthesizing the Same," U.S. Patent 5,973,179 (October 26, 1999).
"A Facile Route to 3-Alkoxy-2-Methylpropenals, Useful Intermediates in the Synthesis of Carotenoids", J.H. Babler, V.P. Liptak, J.A. Trautmann and G.H. Zayia, Synth. Commun., 1996, 26, 1943.
"Alkoxide-Catalyzed Addition of Terminal Alkynes to Ketones", J.H. Babler, V.P. Liptak and N. Phan, J. Org. Chem., 1996, 61, 416.