Stevenson Professor of Chemistry
Ph.D., University of Pennsylvania, 1989
gary.a.sulikowski@vanderbilt.edu
Sulikowski Research Group

Total Synthesis of Natural Products
A major focus of our research group is the synthesis of structurally complex natural products. Frequently, research projects are initiated with the selection of a target structure (recently) isolated from various natural sources such as soil microorganisms, fungi or plants. Criterion for the selection of molecular targets include structural novelty, unique biological activity and/or potential development of a new reaction in assembling a key structural feature contained within the natural product. Target structures of current interest to our group are shown below and represent a broad range of structural complexity and biological activity. Following the identification of a target molecule, researchers, sometimes working as a team, set into action a synthetic strategy aimed at developing an efficient assembly of the targeted structure. It is at this point in the research project that researchers develop critical analysis as well as problem solving skills. Due to the complexity of the synthetic problems we often encounter unforeseen obstacles which require the redesign of the original strategy or the development of a new reaction or modification of an existing process. It is this evolutionary aspect of the synthetic program that leads to new innovations with broader implications in organic synthesis and related areas. Indeed some of the reactions and strategies developed within the context of one natural product have been subsequently applied to other (new) target structures.

Selected Publications

Engers, D.W.; Rodriguez, A.L.; Williams, R.; Hammond, A.S.; Venable, D.; Oluwatola, O.; Sulikowski, G.A.; Conn, P.J.; Lindsley, C.W. Synthesis, SAR and Unanticipated Pharmacological Profiles of Analogues of the mGluR5 Ago-potentiator ADX-47273. ChemMedChem. 2009, 4 (4): 505-511.

Walters, M.J.; Blobaum, A.L.; Kingsley, P.J.; Felts, A.S.; Sulikowski, G.A.; Marnett, L. The influence of double bond geometry in the inhibition of cyclooxygenases by sulindac derivatives. Bioorganic & Medicinal Chemistry Letters. 2009, 19 (12): 3271-3274.

Kim, K.; Miller, N.R.; Sulikowski, G.A.; Lindsley C.W. A new multi-gram synthetic route to labeling precursors for the D-2/3 PET agent F-18-fallypride. Bioorganic & Medicinal Chemistry Letters. 2008, 18 (16): 4467-4469.

Zhang, W.; Baranczak, A.; Sulikowski, G. A. Stereocontrolled Assembly of the C3/C3’ Dideoxy Core of Lomaiviticin A/B and Congeners. Organic Letters. 2008, 10: 1939-1941.

Luo, Z.S.; Peplowski, K.; Sulikowski, G.A. Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction. Organic Letters. 2007, 9 (24): 5051-5054.

Doroh, B.; Sulikowski, G.A. Progress toward the total synthesis of bielschowskysin: A stereoselective [2+2] photocycloaddition. Organic Letters. 2006, 8 (5): 903-906.

Sulikowski, G.A.; Pongdee, R. Elucidation of the Biosynthetic pathway leading to the complex nonadride phomoidride B. Synlett. 2006, (3): 354-363.

Sulikowski, G.A. Synthesis and biology of cell-specific apoptosis inducing agents from nature. Cancer Epidemiology Biomarkers & Prevention. 2005, 14 (11): 2777S-2777S.

Kiewel, K.; Luo, Z.S.; Sulikowski, G.A. Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide. Organic Letters. 2005, 7 (23): 5163-5165.

Jin, B.H.; Liu, Q.S.; Sulikowski, G.A. Development of an end-game strategy towards apoptolidin: a sequential Suzuki coupling approach. Tetrahedron. 2005, 61 (2): 401-408.

Lee, W.D.; Kim, K.; Sulikowski, G.A. Studies into the stereoselectivity of tartrate-derived dienophiles. Organic Letters. 2005, 7 (9): 1687-1689.

Kim, Kwangho; Maharoof, Umar S. M.; Raushel, Jessica; Sulikowski, Gary A. Diverging Stereochemical Pathways in an Intramolecular Diels-Alder Reaction Determined by Dienophile Structure. Organic Letters. 2003, 5: 2777-2780.

Boren, Brant; Hirschi, Jennifer; Reibenspies, Joseph H.; Tallant, Mathew D.; Singleton, Daniel A.; Sulikowski, Gary A. Exo Selective Diels-Alder Reactions of Vinylazepines. Origin of Divergent Stereoselectivity in Diels-Alder Reactions of Vinylazepines, Vinylpiperideines and Vinycyclohexens. Journal of Organic Chemistry. 2003, 68: 8991-8995.

Maharoof, Umar S. M.; Sulikowski, Gary A. Investigations into Arylquinone Atropisomers: Synthesis and Evaluation. Tetrahedron Letters. 2003, 44: 9021-9023.

Lee, Chee-Seng.; Audelo, M. Q.; Reibenspies, Joseph H.; Sulikowski, Gary A. Studies Toward the Total Synthesis of Hibarimicinone.  Progress on the Assembly of the AB- and GH-Ring Systems. Tetrahedron. 2002, 58: 4403-4409.

Sulikowski, Gary A.; Liu, Weidong; Luo, Zhushou; Agnelli, Fabio; Corbett, R. Michael; Hershberger, Stephen J. Progress Towards a Biomimetic Synthesis of Phomoidride B. Organic Letters. 2002, 4: 1451-1454.

Penington, James D.; Williams, Howard J.; Salomon, Arthur R.; Sulikowski, Gary A. Toward a Stable Apoptolidin Derivative: Identification of Isoapoptolidin and Selective Deglycosylation of Apoptolidin. Organic Letters. 2002, 4: 3823-3825.

Pongdee, Rongson; Wu, Bin; Sulikowski, G.A. One-Pot Synthesis of 2-Deoxy-b-oligosaccharides. Organic Letters. 2001, 3: 3523-3525.

Specialties

• VICB
• Organic Chemistry
• Biochemistry

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