White, James D.

Education:
B.A. Cambridge University (1959)
M.Sc. University of British Columbia (1961)
Ph.D. Massachusetts Institute of Technology (1965)

Awards:
Devon County Scholarship, Cambridge University (1956-1959)
Cabot Solar Energy Fellowship, M.I.T. (1962-1963)
National Institutes of Health Predoctoral Fellowship, M.I.T. (1964-1965)
Eli Lilly Grant Award (1968-1969)
National Institutes of Health Research Career Development Award (1976-1981)
Sigma Xi Research Award, Oregon State University Chapter (1981)
Japan Society for the Promotion of Science Fellowship (1983)
Milton Harris Award for Basic Research, Oregon State University (1987)
Guggenheim Fellowship (1988-1989)
Sc.D., Cambridge University (1995)
F. A. Gilfillan Memorial Award, Oregon State University (1996)
Centenary Medal, Royal Society of Chemistry, U.K. (1999)
Wyeth-Ayerst Research Award, Columbia University (2000)
Arthur C. Cope Senior Scholar Award, American Chemical Society (2003)
Oregon Health Science University Foundation Discovery Award (2004)
Oregon Outstanding Scientist Award (2006)
Fellow of the American Chemical Society (2011)

Research Group Web Site:
http://www.chemistry.oregonstate.edu/white

Organic and Bioorganic Web Site:
http://www.chemistry.oregonstate.edu/organic/

Research Interests

My research program blends studies of synthetic methods with the total synthesis of natural products and other complex molecules.  The goal of our work is to develop new strategies in synthesis and then apply them to the elaboration of targets where particular structural features present a significant challenge.

The synthesis of complex, highly functionalized structures often requires new methodology, and a substantial part of my research is devoted to finding new reactions and improving old ones.  I am particularly interested in devising better ways to secure stereochemistry in densely functionalized structural environments, such as that present in the perimeter of certain macrolides, and for this purpose we are developing new chiral reagents which should facilitate asymmetric synthesis of subunits of these structures.  In addition, we seek novel ways to exploit radical chemistry, photochemistry, and enzymes in the synthesis of specific structural motifs found in natural products.

In designing synthetic routes to complex molecules, the plan often incorporates a key step which plays a pivotal role in establishing the molecular framework.  This central reaction may be one patterned after the presumed biogenesis of the compound, or it may be one intended to test the efficiency of a particular bond construction, ring forming process, skeletal rearrangement, etc.  These exercises in synthesis usually have a specific target in mind, but the conciseness and novelty of the route to our objectives is always considered at least as important as reaching the goal.

Representative Publications

• Synthesis of the Cyclohexane Core of Phomactins and a New Route to the Bicyclo[9.3.1]pentadecane Diterpenoid Skeleton. Org. Lett. 2011, 13, 248-251. 
• Cis-2,5-diaminobicyclo [2.2.2]octane, a New Scaffold for Asymmetric Catalysis via Salen-metal complexes.  Org. Lett. 2011, 13, 2488-2491.
• Synthesis and structural characterization of a fused bispyrone and preparation of the first metal bispyryrlium complexes.  Chem. Commun, 2010, 46, 5304-5306. 
• Tandem Intramolecular Photocycloaddition-Retro-Mannich Fragmentation as a Route to Spiro{pyrrolidine-3,3'-oxinidoles].  Total Synthesis of (+/-)-Coerulescine, (+/-)-Horsfiline, (+/-)-Elacomine, and (+/-)-Deoxyelacomine.  J. Org. Chem, 2010, 75, 3569-3577. 
• Synthesis of 1,1-{1-Naphthyloxy-2-thiophenyl}-2-methylaminomethylcyclopropanes and their Evaluation as Dual Inhibitors of Seratonin, Norepinephrine and Dopamine Transporters.  J. Med. Chem, 2009, 52, 5872-5879. 
• Synthesis of the northern sector (CS-C19) of rapamycin via Chan rearrangement and oxidation of an α-acyloxyacetate.  Tetrahedron, 2009, 65, 6642-6647. 
• Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressents FK-506 and rapamycin.  Tetrahedron, 2009, 65, nn6635-6641. 
• Synthesis of the Cyclobutylfuran Sector of Providencin via Zirconium-mediated Oxygen Abstraction from a Furanoside.  Org. Lett, 2009, 11, 1433-1436. 
• Strategies for the Synthesis of the Cyclopropyl Lactone Family of Oxylipins.  Synlett, 2009, 1713-1729. 
• Synthesis of an Advanced Intermediate for (+)-Pillaromycinone.  Staunton-Weinreb Annulation Revisited, Org. Lett. 2008, 10, 2833-2836. 
• Total Synthesis of Solandelactones A, B, E and F. Exploiting a Tandem Petasis-Claisen Lactonization Strategy. J. Org. Chem., 2008, 73, 4139-4150.
• Total Synthesis of Solandelactones E and F, Homoeicosanoids from the Hydroid Solanderia secunda, Org. Lett., 2007, 9 (17), 3481-3483.
• A New Route to Furanoeremophilane Sesquiterpenoids. Synthesis of Senecio Metabolites (±)-6-Hydroxyeuryopsin, (±)-1,10-Epoxy-6-hydroxyeuryopsin, (±)-Toluccanolide A and (±)-Tolucannolide C, Org. Biomol. Chem., 2006, 4, 1020-1031.
• The Synthesis of Polycavernoside A. An Example of Conformationally Guided Macrolactonization.  In Strategies and Tactics in Organic Synthesis, Harmata, M., Ed. Elsevier, Vol. 4., 2005, Vol. 6, pp. 173-210.
• Application of the Dötz Reaction to Construction of a Major Portion of the Ansa Macrocycle (-)-Kendomycin, Org. Lett. 2005, 7 (2), 235-238.
• Total Synthesis of (-)-7-Epicylindrospermopsin, a Toxic Metabolite of the Freshwater Cyanobacterium Aphanizomenon ovalisporum, and Assignment of Its Absolute Configuration J. Org. Chem. 2005, 70, 1963-1977.
• Total Synthesis and Biological Evaluation of (+)-Kalkitoxin, a Cytotoxic Metabolite of the Cyanobacterium Lyngbya majuscula, Org. Biomol. Chem. 2004, 2, 2092-2102.
• Stereochemistry of contiguous cyclopropane formation from cascade cyclization of a skipped dienyl homoallyl triflate, Chem. Commun., 2004, 2846-2847.
• Total Synthesis of Rhizoxin D, a Potent Antimitotic Agent from the Fungus Rhizopus chinensis, J. Org. Chem. 2002, 67 7750-7760.