Scott D. RychnovskyProfessor, Chemistry |
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Research Interests |
Organic Chemistry | |
| URL | www.chem.uci.edu/~srychnov/Rychnovsky.html | |
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Academic Distinctions |
Arthur C. Cope Scholar Award Fresenius Award Zeneca Chemistry Award Searle Scholar Fellow Camille and Henry Dreyfus Foundation Teacher-Scholar Eli Lilly Fellow Pfizer Research Award in Synthetic Organic Chemistry Alfred P. Sloan Fellow National Science Foundation Presidential Young Investigator Award S. T. Li Prize for Achievements in Science and Technology Associate Editor for The Journal of Organic Chemistry |
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| Appointments |
NIH Postdoctoral Fellow, Harvard University Faculty member at the University of Minnesota from 1988-1995 Joined UCI faculty in 1995 |
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Research Abstract |
New methods are at the heart of synthetic organic chemistry. We are developing new methods to form carbon-carbon bonds and to introduce stereogenic centers. For example, we are investigating the Prins cyclization reaction, in which a new ring is formed along with a carbon-carbon bond and up to three new stereogenic centers. The potential of this reaction is further enhanced by our recent observation that carbon nucleophiles will participate and trap the penultimate carbenium ion. The use of carbon nucleophiles leads to a rapid increase structural complexity. Our new methodology is developed in the context of natural product total synthesis. Natural products present a myriad of interesting and diverse structural types that continue to challenge the synthetic chemist. Given the tremendous advances in methods development over the last few decades, almost any natural product could be made by talented synthetic chemists, but often only after many person-years of painstaking labor. Our methods are designed to make the synthesis of targeted natural products much more rapid and efficient. We select synthetic targets based on interesting structural features and unusual biological activity. These synthetic targets are a focus for our new methods and provide a challenge against which to measure their effectiveness. Specific natural products of interest include rimocidin, phorboxazole A, epicalyxin F, and leucascandrolide A. |
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| Publications | Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol-Prins Reaction. Lori J. Van Orden, Brian D. Patterson, and Scott D. Rychnovsky, J. Org. Chem. 2007, 72, 5784-5793 | |
| A Reductive Cyclization Approach to Attenol A. Thomas E. La Cruz and Scott D. Rychnovsky, J. Org. Chem. 2007, 72, 2602-2611. | ||
| Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal. Danielle Vellucci and Scott D. Rychnovsky, Org. Lett. 2007, 9, 711-714. | ||
| Synthesis of the C31C67 Fragment of Amphidinol 3. Javier de Vicente, John R. Huckins, and Scott D. Rychnovsky, Angew. Chem., Int. Ed. 2006, 45, 7258-7262. | ||
| Racemization in Prins Cyclization Reactions. Ramesh Jasti and Scott D. Rychnovsky, J. Am. Chem. Soc. 2006, 128, 13640-13648. | ||
| Predicting NMR Spectra by Computational Methods: Structure Revision of Hexacyclinol. Scott D. Rychnovsky, Org. Lett. 2006, 8, 2895-2898. | ||
| Total Synthesis and Structural Confirmation of (+)-Hexacyclinol. John A. Porco, Jr., Shun Su, Xiaoguang Lei, Sujata Bardhan, and Scott D. Rychnovsky, Angew. Chem., Int. Ed. 2006, 45, 5790-5792. | ||
| Rapid Stereocontrolled Assembly of the Fully Substituted C-Aryl Glycoside of Kendomycin with a Prins Cyclization: A Formal Synthesis. Kevin B. Bahnck and Scott D. Rychnovsky, Chem. Commun. 2006, 2388-2390. | ||
| Synthesis and Structure Revision of Calyxin Natural Products. Xia Tian, James J. Jaber and Scott D. Rychnovsky, J. Org. Chem. 2006, 71, 3176-3183. | ||
| Tetrahydropyran Rings from a Mukaiyama-Michael Cascade Reaction. Megan L. Bolla, Brian Patterson, and Scott D. Rychnovsky, J. Am. Chem. Soc. 2005, 127, 16044-16045. | ||
| Utilization of an Oxonia-Cope Rearrangement as a Mechanistic Probe for Prins Cyclizations. Ramesh Jasti, Christopher D. Anderson, and Scott D. Rychnovsky, J. Am. Chem. Soc. 2005, 127, 9939-9945. | ||
| Synthesis of the Spirofungin B Core by a Reductive Cyclization Strategy. Thomas E. La Cruz and Scott D. Rychnovsky, Org. Lett. 2005, 7, 1873-1875. | ||
| Dual Roles for Cholesterol in Mammalian Cells. Fang Xu, Scott D. Rychnovsky, Jitendra D. Belani, Helen H. Hobbs, Jonathan C. Cohen, and Robert B. Rawson, PNAS, 2005, 102, 14551-14556. | ||
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Professional Society |
American Chemical Society |
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| Other Experience |
Professor Univeristy of Minnesota 1988—1995 |
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| Link to this profile | http://www.faculty.uci.edu/profile.cfm?faculty_id=2092 | |
| Last updated | 08/11/2007 | |
