Beaudry, Chris

Vicki and Patrick F. Stone Scholar

Education:
B. S. (2000) University of Wisconsin; 
Ph.D. (2005) University of California - Berkeley; 
Postdoctoral Fellow (2006 - 2009) University of California - Irvine

Research Group Website: http://chemistry.oregonstate.edu/beaudry/

Research Interests

The rich structural diversity, intriguing molecular architectures, and potent biological activities of natural products make these compounds compelling targets for synthesis. However, chemists remain limited by the available methods for the efficient construction of many structural motifs.

Research in my group is directed at developing new methods to address these limitations. The approach seeks to conceptualize the most strategically powerful simplification of the target, giving rise to readily available starting materials.  This simplification will often demand methodology which does not currently exist, but would have widespread application.  Once developed, we will use these methods for the synthesis of a variety of complex natural products.  Specific areas of interest include nitrogen-rich alkaloids, enantioselective catalysis, chirality of organic molecules, cascade processes, radical reactions, and organometallic chemistry.

Representative Publications

1.  "Desymmetrization by Ring-Closing Metathesis Leading to 6,8-Dioxabicyclo[3.2.1]octanes: A New Route of the Synthesis of (+)-exo- and endo- Brevicomin." Burke, S.D.; Muller, N.; Beaudry, C.M.  Org. Lett.  1999, 1, 1827-1829.

2.  "Synthetic Studies Toward SNF4435 C and SNF4435 D."  Beaudry, C.M.; Trauner, D.  Org. Lett. 2002, 4, 2221-2224.

3.  "Intramolecular Diels-Alder Reactions of 5-Vinyl-1,3-cyclohexadienes."  Ng, S.M; Beaudry, C. M; Trauner, D.  Org. Lett. 2003, 5, 1701-1704

4.  "9-(Anthrylmethyl)-trimethylammonium chloride monohydrate."  Beaudry, C.M.; Pehl, J.; Wovkulich, K.M.  Acta. Cryst., Sect. E. 2003, E59, o897-o898.

5.  "Development of Novel Lewis Acid Catalyzed Cycloisomerizations: Synthesis of Bicyclo[3.1.0]hexenes and Cyclopentenones."  Miller, A.K.; Banghart, M.R.; Beaudry. C.M.; Suh, J.K.; Trauner, D.  Tetrahedron 2003, 59, 8919-8930.

6.  "The Total Synthesis of (-)-Crispatene."  Miller, A.K.; Byun, D.H.; Beaudry, C.M.; Tauner, D.  Proc. Natl. Acad. Sci. USA 2004, 101, 12019-12023.

7.  "Dienophile Twisting and Substituent Effects Influence Reaction Rates of Intramolecular Diels-Alder Cycloadditions: A DFT Study."  Khuong, K.S.; Beaudry, C.M.; Trauner, D.; Houk, K.N.  J. Am. Chem. Soc.  2005, 127, 3688-3689.

8.  "Biosynthetic and Biomimetic Electrocyclizations."  Beaudry, C.M.; Malerich, J.P.; Trauner, D.  Chem. Rev.  2005, 105, 2757-2778.

9.  "Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D." Beaudry, C.M.; Trauner D.  Org. Lett. 2005, 7, 4475-4477. 

10.  "Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through 'Polyene slicing'." Mueller, M.; Kusenbauch, B.; Liang, G.; Beaudry, C.M.; Trauner, D.; Hertweck, C. Angnew. Chem. Int. Ed. 2006, 45, 7835-7838.

11.  "Golgi Modifying Properties of Macfarlandin E and the Synthesis and Evaluation of Its 2,7-Dioxabicyclo[3.2.1]octan-3-one Core." Schnermann, M.J.; Beaudry, C.M.; Egorova, A. V.; Polishchuck, R.S.; Overman, L.E.; Suetterlin, C.  Proc. Natl. Acad. Sci. USA 2010, 107, 6158-6163.