McIntosh, Matt - University of Arkansas-Fayetteville

个人简介

American Cancer Society Postdoctoral Fellow, Stanford University 1993-96 Ph.D., The Pennsylvania State University, 1993 B.A., Virginia Tech, 1987

研究领域

natural product synthesis The McIntosh research group is involved in synthetic organic chemistry, including both synthetic methods development and total synthesis of complex natural products. Current targets include sclerophytin-A, massileunicellin-I and antascomicin-B. Natural product total synthesis is the reconstruction of a naturally occurring compound in the laboratory starting from simple, commercially available materials. There are several goals of natural products total synthesis: - Prove or disprove the proposed structure of the natural product - Provide additional quantities of the natural product for biological testing - Learn the unique chemistry of the natural product - Modify the natural product to improve its biological profile, e.g. improve potency, decrease side effects, increase metabolic stability, increase solubility, etc. - Discover new organic chemistry In the course of our investigations, we have developed a number of new variants of organic reactions, including the Claisen rearrangement, the allylic diazene rearrangement, and the cycloaldol reaction. For more detailed information on these and other projects in the McIntosh group, visit the group home page (link below).

近期论文

查看导师新发文章（温馨提示：请注意重名现象，建议点开原文通过作者单位确认）

Intercepting the Breslow Intermediate via Claisen Rearrangement: Synthesis of Complex Tertiary Alcohols without Organometallic Reagents Sefat Alwarsh, Kolawole Ayinuola, Silvana Dormi and Matthias C. McIntosh Org. Lett. 2013, 15, 3-5. Highlighted in Organic Process Research & Development, 2013, 17, p607 DOI: 10.1021/op400064j Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds David R. Clay and Matthias C. McIntosh Tetrahedron Lett. 2012, 53, 1961-4. Synthesis of the C21-C34 fragment of antascomicin B John M. Hutchison, Andrew S. Gibson, David T. Williams and Matthias C. McIntosh Tetrahedron Lett. 2011, 52, 6349-6351. Efficient, scalable asymmetric synthesis of an epoxy quinol via Noyori desymmetrization of a meso diketone David R. Clay, Ashley G. Rosenberg and Matthias C. McIntosh Tetrahedron: Asymmetry 2011, 22, 713-6 . Studies directed toward the synthesis of the massileunicellins. Part 2 Yonghai Chai, Zonghong Mou and Matthias C. McIntosh Tetrahedron. Lett. 2010, 51, 2393-5. Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans T. David Bateman, Aarti Joshi, Kwangyul Moon, Elena N. Galitovskaya, Meenakshi Upreti, Timothy C. Chambers and Matthias C. McIntosh Biorg. Med. Chem. Lett. 2009, 19, 6898-6901. Total Synthesis: From Chemistry to Medicine A 20-minute documentary style film produced by Matt McIntosh, David Clay, and Kathy Gearhart ©2009 Toward the synthesis of antascomicin B. Synthesis of a model of the C22–C34 fragment via Ireland–Claisen and allylic diazene rearrangements Wei Qi and Matthias C. McIntosh Tetrahedron. 2008, 64, 7021-5. Acyclic 1,4-Stereocontrol via Reductive 1,3-Transpositions Wei Qi and Matthias C. McIntosh Org. Lett. 2008, 10, 357-9. The Ireland-Claisen Rearrangement (1972-2004) Christopher M. McFarland and Matthias C. McIntosh in The Claisen Rearrangement: Methods and Applications, M. Hiersemann and U. Nubbemeyer, Eds.; Wiley Interscience, Weinheim; 2007. Approach to the Synthesis of Cladiell-11-ene-3,6,7-triol John M. Hutchison, Harriet A. Lindsay, Silvana S. Dormi, Gavin D. Jones, David A. Vicic and Matthias C. McIntosh Org. Lett. 2006, 8, 3663-5. Unprecedented Alkene Stereocontrol in the Claisen Rearrangement of Cyclic Bis-Allylic Esters Chris McFarland, John Hutchison and Matthias C. McIntosh Org. Lett. 2005, 7, 3641-4. Improved Alkylation and Product Stability in Phosphotriester Formation through Quinone Methide Reactions with Dialkyl Phosphates Brian Bakke, Matthias C. McIntosh and Kenneth D. Turnbull J. Org. Chem. 2005, 70, 4338-45. Convenient 3-Step Synthesis of (R)-7-Hydroxycarvone from (S)-a-Pinene Rajamma Lakshmi, T. David Bateman and Matthias C. McIntoshJ. Org. Chem. 2005, 70, 5313-5. An Ireland-Claisen Approach to Lignans: Synthesis of the Putative Structure of 5-epi-Eupomatilone-6 John M. Hutchison, Sang-phyo Hong and Matthias C. McIntosh J. Org. Chem., 2004, 69, 4185-4191. Studies Directed Toward the Synthesis of the Massileunicellins Yonghai Chai and Matthias C. McIntosh Tetrahedron. Lett., 2004, 45, 3269-3272. Cycloaldol Approach to the Isobenzofuran Core of the Eunicellin Diterpenes Yonghai Chai, David A. Vicic and Matthias C. McIntosh Org. Lett., 2003, 7, 1039-1042. New Aspects of the Ireland and Related Claisen Rearrangements Yonghai Chai, Sang-phyo Hong, Harriet A. Lindsay, Chris McFarland and Matthias C. McIntosh Tetrahedron, 2002, 58, 2905-2928. Intramolecularly Competitive Ireland Claisen Rearrangements: Scope and Potential Applications to Natural Product Synthesis Sang-Phyo Hong, Harriet A. Lindsay, Tripura Yaramasu, Xiaowei Zhang and Matthias C. McIntosh J. Org. Chem. 2002, 67, 2042-2055. An Approach to the Synthesis of the Eupomatilones Sang-pho Hong and Matthias C. McIntosh, Org. Lett. 2002, 4, 19-21.