DRURY S. CAINE Professor Emeritus ORGANIC CHEMISTRY total synthesis of natural products of medical importance, enolate and dienolate chemistry, dienone photochemistry B.A., 1954; M.S., 1956, Vanderbilt University; Ph.D., 1961, Emory University; NIH Postdoctoral Fellow, 1961, Columbia University. office: 243D Shelby Hall Telephone: (205) 348-8454 fax (205) 348-9104

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Research Interests

Professor Caine is primarily interested in the total synthesis of naturally occurring compounds, particularly sesquiterpenes, diterpenes and butenolides, which are of medicinal interest. He is also interested in photochemical rearrangements of cross-conjugated cyclohexadienones and related compounds, the formation and reactions of metal enolates and homoenolates of saturated and unsaturated ketones and carboxylic acid derivatives, heterosubstituted vinyllithium reagents, reductive cleavage and other reactions of conjugated cyclopropyl ketones, retroaldol reactions of cycloalkanone derivatives and cycloaddition reactions of dienolates of 3(2H)-furanones and related compounds.

Some past projects of Professor Caine's research group include a photochemical approach to the synthesis of thapsigargin, a calcium ATPase inhibitory sesquiterpene, and a reinvestigation of the in vitro reactions of streptozotocin, a diabetogenic agent, related to glucosamine.

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Representative Publications

"Reactions of Conjugated Haloenoates with Nucleophilic Reagents," D. Caine, Tetrahedron 57, 2643 (2001).

"Reactions of a 3(2H)-Furanone Lithium Enolate with 4-Halocrotonates" D. Caine and M. A. Paige, Synlett 1391, (1999).

"Reactions of Lithium Dienolates of 2,5-Dimethyl-3(2H)-furanone with Unsaturated Compounds," D. Caine and R. F. Collison, Synlett 503 (1995).

"Photochemical Rearrangements of 6/6- and 6/5-Fused Cross-Conjugated Cyclohexadienones," D. Caine, in Handbook of Organic Photochemistry and Photobiology W. M. Horspool, Ed., CRC: Boca Raton, Florida (1995).

"The Synthesis of 11-Oxabicyclo[6.2.1]undecenone Derivatives," D. Caine and M. E. Arant, Tetrahedron Lett. 35, 6795 (1994).

"A Convenient Synthesis of 7,9,9-Trimethyl-1-oxaspiro[4,5]-6-decen-2-one," D. Caine and C.-Y. Lin, Synth. Commun. 24, 2473 (1994).

"Introduction of an Isopropyl Group at the Gamma Position of a Hydrindenone Derivative," D. Caine and P. L. Kotian, Synth. Commun.24, 2039 (1994).

"Synthesis and Photochemical Rearrangements of 1(R), 7a(S)-1-tert-Butyldiphenylsiloxy)-7a-methyl-5(7aH) -indanone," D. Caine and P. L. Kotian, J. Org. Chem. 57, 6587 (1992).

"Synthesis and Photochemical Rearrangements of Bicyclic Cross-Conjugated Cyclohexadienones Containing d-Oxy Substituents," D. Caine, P. L. Kotian, and M. D. McGuiness, J. Org. Chem. 56, 6307 (1991).

"Alkylations of Enols and Enolates," D. Caine in "Comprehensive Organic Synthesis", Volume 3, G. Pattenden, Ed., Pergamon: New York, Chapter 1 (1991).

"Wharton Fragmentations of Cyclic 1,3-Diol Derivatives," D. Caine, Org. Prep. Proc. Int. 20, 1, (1988).

"Stereochemical Aspects of the Reaction of Lithio(1-methyl-2-propenyl) diphenylphosphine Oxide with b-Substituted Aldehydes. Short Synthesis of (-)-a-Selinene and (+)-a-Helmiscapene," D. Caine, B. Stanhope, and S. Fiddler, J. Org. Chem. 53, 4124 (1988).

The University of Alabama Department of Chemistry Faculty