total synthesis of natural products of medical importance,
enolate and dienolate chemistry, dienone
B.A., 1954; M.S.,
1956, Vanderbilt University; Ph.D., 1961, Emory University;
NIH Postdoctoral Fellow, 1961, Columbia
office: 2058 Shelby Hall
Telephone: (205) 348-8454
fax (205) 348-9104
Professor Caine is
primarily interested in the
total synthesis of naturally occurring
particularly sesquiterpenes, diterpenes and butenolides, which are of
medicinal interest. He is also interested in
cross-conjugated cyclohexadienones and related compounds,
formation and reactions of metal enolates and
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.
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
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).
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
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
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
"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).
University of Alabama Department of Chemistry