个人简介

B.S. 1973, University of Wisconsin-Eau Claire Ph.D. 1978, University of Pittsburgh .

研究领域

Organic/Organic

Our primary research interests focus on synthetic organic chemistry, with an emphasis on the efficient synthesis of natural products (and analogues thereof) with potent biological activity. Development of synthetic methods and novel strategies in response to the demands of complex molecule construction are key elements of our approach to target-oriented synthesis. Exemplifying this is our ongoing exploitation of symmetry for simplification of synthetic sequences, with the accompanying need for methods to efficiently break symmetry. Recently completed syntheses of such diverse structural types as phorboxazole B, thromboxane B2, didemniserinolipid B, squamocin N, and dictyostatin illustrate common themes that have been developed in our group. Included among these themes are Pd(0)-mediated asymmetric double cycloetherification, ketalization/ring-closing metathesis, asymmetric double hetero Diels-Alder cycloaddition, and kinetically-controlled Meerwein-Ponndorf-Verley reduction. A substantial portion of our current efforts are directed at developing Rh-catalyzed asymmetric hydroformylations (AHF) in tandem with compatible C-C and C-X bond forming reactions. We are pursuing this endeavor in collaboration with the Landis group, seeking to explore the possibility of using the chiral bis(diazaphospholane) [“BDP”] ligand/Rh(I) catalysts in complex molecule synthesis. The perfectly atom-economical AHF procedure delivers branched, chiral aldehydes in high enantiomeric excess from achiral alkenes, CO, and H2, with very low catalyst loadings. An illustrative example of the power of these tandem processes to facilitate complex natural product synthesis is shown in the scheme below, detailing a 4-step synthesis of the C1-C7 subunit of the methynolide antibiotics (see numbered structure of the natural product in 1st box). Beginning with the AHF of commercially available acrolein acetal, the branched aldehyde formed is directly reacted with the indicated E-crotyltrifluorborate to afford a stereotriad in a highly enantio- and diastereoselective manner. Acylation and Ru-catalyzed ring-closing metathesis provided the unsaturated d-lactone, which was reduced to the boxed C1-C7 subunit.

近期论文

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Lucas, Brian S.; Luther, Laura M.; Burke, Steven D.. A Catalytic Enantioselective Hetero Diels-Alder Approach to the C20-C32 Segment of the Phorboxazoles. Journal of Organic Chemistry 2005, 70, 3757-3760 Lambert, William T.; Hanson, Gregory H.; Benayoud, Farid; Burke, Steven D.. Halichondrin B: Synthesis of the C1-C22 Subunit. Journal of Organic Chemistry 2005, 70, 9382-9398 Keller, Valerie A.; Kim, Ikyon; Burke, Steven D.. Synthetic Efforts toward the C22-C36 Subunit of Halichondrin B Utilizing Local and Imposed Symmetry. Organic Letters 2005, 7, 737-740 Voight, Eric A.; Roethle, Paul A.; Burke, Steven D.. Concise Formal Synthesis of the Bryostatin Southern Hemisphere (C17-C27). Journal of Organic Chemistry 2004, 69, 4534-4537 Jiang, Yueheng; Hong, Jian; Burke, Steven D.. Stereoselective Total Synthesis of Antitumor Macrolide (+)-Rhizoxin D. Organic Letters 2004, 6, 1445-1448 Voight, Eric A.; Seradj, Hassan; Roethle, Paul A.; Burke, Steven D.. Synthesis of the Bryostatin 1 Northern Hemisphere (C1-C16) via Desymmetrization by Ketalization/Ring-Closing Metathesis. Organic Letters 2004, 6, 4045-4048 Lucas, Brian S.; Luther, Laura M.; Burke, Steven D.. Synthesis of the C1-C17 Segment of Phorboxazole B. Organic Letters 2004, 6, 2965-2968 Guzei, Ilia A.; Clark, Robert W.; Burke, Steven D.; Lambert, William T. A comparison of the ring conformational properties of two derivatives prepared from the same diene diacetate precursor. Acta Crystallographica, Section C: Crystal Structure Communications 2003, C59, o721-o723 Jiang Lei; Martinelli Joseph R; Burke Steven D A practical synthesis of the F-ring of halichondrin B via ozonolytic desymmetrization of a C(2)-symmetric dihydroxycyclohexene. The Journal of organic chemistry 2003, 68, 1150-3 Lambert, William T.; Burke, Steven D.. Halichondrin B: Synthesis of a C1-C14 Model via Desymmetrization of (+)-Conduritol E. Organic Letters 2003, 5, 515-518 Lucas, Brian S.; Burke, Steven D.. Palladium(0)-Mediated Desymmetrization of Meso Tetraols: An Approach to the C3-C17 Bis-oxane Segment of Phorboxazoles A and B. Organic Letters 2003, 5, 3915-3918 Jiang Lei; Burke Steven D A novel route to the F-ring of halichondrin B. Diastereoselection in Pd(0)-mediated meso and C(2) biol desymmetrization. Organic letters 2002, 4, 3411-4 Keller, Valerie A.; Martinelli, Joseph R.; Streiter, Eric R.; Burke, Steven D.. Dioxolane-to-Bridged Acetal-to-Spiroketal via Ring-Closing Metathesis and Rearrangement: A Novel Route to 1,7-Dioxaspiro[5.5]undecanes. Organic Letters 2002, 4, 467-470 Austad, Brian C.; Hart, Amy C.; Burke, Steven D.. Halichondrin B: synthesis of the C(37)-C(54) subunit. Tetrahedron 2002, 58, 2011-2026 Campbell John E; Englund Erikah E; Burke Steven D Synthesis and structure of preorganized, C(3)-symmetric trilactam scaffolds with convergently oriented (S)-acetylthiomethyl appendages. Organic letters 2002, 4, 2273-5 Voight, Eric A.; Rein, Christian; Burke, Steven D.. Synthesis of Sialic Acids via Desymmetrization by Ring-Closing Metathesis. Journal of Organic Chemistry 2002, 67, 8489-8499 Burke, Steven D.; Voight, Eric A. Formal Synthesis of (+)-3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) via Desymmetrization by Ring-Closing Metathesis. Organic Letters 2001, 3, 237-240 Voight, Eric A.; Rein, Christian; Burke, Steven D.. Formal synthesis of (-)-N-acetylneuraminic acid (Neu5Ac) via desymmetrization by ring-closing metathesis. Tetrahedron Letters 2001, 42, 8747-8749 Burke, Steven D.; Jiang, Lei. Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization. Organic Letters 2001, 3, 1953-1955 Clark, Robert W.; Guzei, Ilia A.; Ivanov, Sergei A.; Burke, Steven D.; Lambert, William T. The lack of C2 molecular symmetry in (1R,2R,3S,6S)-3,6-dibenzyloxycyclohex-4-ene-1,2-diol. Acta Crystallographica, Section C: Crystal Structure Communications 2001, C57, 844-845