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Scott D. Rychnovsky

Professor, Chemistry
School of Physical Sciences

PH.D., Columbia University, 1986


B.A. 1981, University of California at Berkeley

Phone: (949)824-8292
Fax: (949) 824-6379
Email: srychnov@uci.edu

University of California, Irvine
3038B FRH
Mail Code: 2025
Irvine, CA 92697

picture of Scott D. Rychnovsky

Research
Interests
Organic Chemistry, Synthesis and Structure Determination
   
URL Group Website
   
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

Fellow of the American Association for the Advancement of Science

Fellow of the American Chemical Society
   
Appointments NIH Postdoctoral Fellow, Harvard University

Faculty member at the University of Minnesota from
1988-1995
Joined UCI faculty in 1995
   
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.
   
Available Technologies
Publications Nanomole-scale Assignment of Configuration for Primary Amines Using a Kinetic Resolution Strategy. Shawn M. Miller, Renzo A. Samame and Scott D. Rychnovsky, J. Am. Chem. Soc. 2012, 134, 20318-20321.
   
  Mapping the structural topology of the yeast 19S proteasomal regulatory particle using chemical cross-linking and probabilistic modeling. Athit Kao, Arlo Randall, Yingying Yang, Vishal R. Patel, Wynne Kandur, Shenheng Guan, Scott D. Rychnovsky, Pierre Baldi, and Lan Huang, Mol. Cell. Proteomics 2012, 11, Epub. (DOI: 10.1074/mcp.M112.018374)
   
  Total Synthesis of Lepadiformine Alkaloids using N-Boc Alpha-Amino Nitriles as Trianion Synthons. Matthew A. Perry, Matthew D. Morin, Brian W. Slafer and Scott D. Rychnovsky, J. Org. Chem. 2012, 77, 3390-3400.
   
  Development of a Novel Cross-Linking Strategy for Fast and Accurate Identification of Cross-Linked Peptides of Protein Complexes. Athit Kao, Chi-li Chiu, Danielle Vellucci, Yingying Yang, Shenheng Guan, Arlo Randall, Pierre Baldi, Scott D. Rychnovsky, Lan Huang, Mol. Cell. Proteomics 2011, 10, 1-17.
   
  Total Synthesis of the Cyanolide A Aglycon. Mike R. Gesinski and Scott D. Rychnovsky, J. Am. Chem. Soc. 2011, 133, 9727-9729.
   
  A Concise Synthesis of ent-Cholesterol. Jitendra D. Belani and Scott D. Rychnovsky, J. Org. Chem. 2008, 73, 2768-2773.
   
  Determination of Absolute Configuration Using Kinetic Resolution Catalysts. Alexander J. Wagner, Jonathan G. David, and Scott D. Rychnovsky, Org. Lett. 2011, 13, 4470-4473.
   
  Fully Substituted Carbon Centers By Diastereoselective Spirocyclization: Stereoselective Synthesis of (+)-Lepadiformine A. C. Matthew Perry, Matthew D. Morin, Brian W. Slafer, Scott A. Wolckenhauer and Scott D. Rychnovsky, J. Am. Chem. Soc. 2010, 132, 9591-9593.
   
  Allyl Transfer to Aldehydes and Ketones by Brønsted Acid Activation of Allyl and Crotyl 1,3,2-Dioxazaborolidines A. Maureen K. Reilly and Scott D. Rychnovsky, Org. Lett. 2010, 12, 4892-4895.
   
  Total Synthesis of (–)-Lycoperine A. Yoshitaka Nakamura, Anthony M. Burke, Shunsuke Kotani, Joseph W. Ziller and Scott D. Rychnovsky, Org. Lett. 2010, 12, 72-75.
   
  Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy. Michael R. Gesinski, Kwanruthai Tadpetch, and Scott D. Rychnovsky, Org. Lett. 2009, 11, 5342-5345.
   
  Polyol Synthesis with beta-Oxyanionic Alkyllithium Reagents: Syntheses of Aculeatins A, B and D. Viengkham Malathong and Scott D. Rychnovsky, Org. Lett. 2009, 11, 4220-4223.
   
  Rhenium(VII) Catalysis of Prins Cyclization Reactions. Kwanruthai Tadpetch and Scott D. Rychnovsky, Org. Lett. 2008, 10, 4839-4842.
   
  Cyclization via Carbolithiation of alpha-Amino Alkyllithium Reagents. Robert J. Bahde and Scott D. Rychnovsky, Org. Lett. 2008, 10, 4017-4020.
   
  Formal Synthesis of (–)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle. Kevin B. Bahnck and Scott D. Rychnovsky, J. Am. Chem. Soc. 2008, 130, 13177-13181.
   
  Assignment of Absolute Configuration to SCH 351448 via Total Synthesis. Lael L. Cheung, Shinji Marumoto, Christopher D. Anderson and Scott D. Rychnovsky, Org. Lett. 2008, 10, 3101-3104.
   
  Lewis Acid-Promoted Mukaiyama Aldol–Prins (MAP) Cyclizations of Acetals, Ketals, alpha-Acetoxy Ethers, and Orthoformates. Michael R. Gesinski, Lori J. Van Orden and Scott D. Rychnovsky, Synlett 2008, 363-366.
   
  Synthesis of the C1-C52 Fragment of Amphidinol 3, Featuring a α-Alkoxy Alkyllithium Addition Reaction. John R. Huckins, Javier de Vicente and Scott D. Rychnovsky, Org. Lett. 2007, 9, 4757-4760.
   
  Synthesis and Structural Reassignment of (+)-Epicalyxin F. Xia Tian and Scott D. Rychnovsky, Org. Lett. 2007, 9, 4955-4958.
   
  Synthesis and Structure Revision of Calyxin Natural Products. Xia Tian, James J. Jaber and Scott D. Rychnovsky, J. Org. Chem. 2006, 71, 3176-3183.
   
  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.
   
  Predicting NMR Spectra by Computational Methods: Structure Revision of Hexacyclinol. Scott D. Rychnovsky, Org. Lett. 2006, 8, 2895-2898.
   
  Total Synthesis and Structural Assignment of (+)-Hexacyclinol. John A. Porco, Jr., Shun Su, Xiaoguang Lei, Sujata Bardhan, and Scott D. Rychnovsky, Angew. Chem., Int. Ed. 2006, 45, 5790-5792.
   
  Racemization in Prins Cyclization Reactions. Ramesh Jasti and Scott D. Rychnovsky, J. Am. Chem. Soc. 2006, 128, 13640-13648.
   
Professional
Society
American Chemical Society
   
Other Experience Professor
Univeristy of Minnesota 1988—1995

   
Link to this profile http://www.faculty.uci.edu/profile.cfm?faculty_id=2092
   
Last updated 01/04/2013