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Scripps Research Joint Appointments

Faculty, Kellogg School of Science and Technology

Research Focus

A central focus of modern synthetic organic chemistry is the design of new reactions and synthesis strategies that will facilitate the construction of complex molecules. We are interested in developing fundamental approaches to the assembly of stereochemically dense architecture that have the potential to facilitate investigations aimed at discovery of biologically active small molecules. Areas of active investigation include the development of new convergent C–C bond forming reactions and the application of these methods to target- and diversity-oriented synthesis.

Alongside these efforts, scientific studies embrace the application of our emerging methods and synthesis strategies to the discovery of novel small molecules of therapeutic relevance.  These studies span:

1) investigations of natural products, and
2) the design and synthesis of diverse collections of synthetic oligomers.  

This latter area of interest aims to establish a foundation of chemistry that, in collaboration with neighboring laboratories at the Scripps Research Institute, is suitable to realize a general biomimetic strategy for the discovery of novel small molecule tools and therapeutic leads.

Education

B.S., Chemistry, Ramapo College of New Jersey, 1996
Ph.D., Chemistry, University of Michigan, 2001

Professional Experience

Associate Professor, Department of Chemistry, The Scripps Research Institute: 2008-present
Assistant Professor, Department of Chemistry, Yale University:2003-2008
Postdoctoral Fellow of the Helen Hay Whitney Foundation, Department of Chemistry and Chemical Biology, Harvard University:2001-2003
PhD, University of Michigan (Rackham Predoctoral Fellow; ACS Division of Organic Chemistry Fellow):1997-2001
BS, Ramapo College of New Jersey:1992-1996

Awards & Professional Activities

University of Michigan Department of Chemistry Kasimir Fajans Award, 2007
Boehringer Ingelheim New Investigator Award, 2007
Yale University Junior Faculty Fellowship in the Natural Sciences, 2006
Lilly Grantee Award, 2006
American Cancer Society Research Scholar Award, 2006
Beckman Young Investigator Award, 2005
Lilly New Faculty Award, 2003
Helen Hay Whitney Postdoctoral Fellowship, 2001-2003
Rackham Predoctoral Fellowship, 2000-2001
American Chemical Society Division of Organic Chemistry Graduate Fellowship, 1999-2000
Roche Award for Excellence in Organic Chemistry, 1999

Selected References

D. Yang, G. C. Micalizio “Synthesis of Alkaloid (–)-205B via Stereoselective Reductive Cross-Coupling and Intramolecular [3+2] Annulation” J. Am. Chem. Soc. 2012, 134, accepted.

P. S. Diez, G. C. Micalizio “Convergent Synthesis of Deoxypropionates” Angew. Chem. Int. Ed. 2012, 51, 5152-5156.

S. Greszler, H. A. Reichard, G. C. Micalizio, “Asymmetric Synthesis of Dihydroindanes by Convergent Alkoxide-Directed Metallacycle-Mediated Bond Formation” J. Am. Chem. Soc. 2012, 134, 2766-2774.

M. Z. Chen, G. C. Micalizio “Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines” J. Am. Chem. Soc. 2012, 134, 1352-1356.

C. Aquino, M. Sarkar, M. J. Chalmers, K. Mendez, T. Kodadek, G. C. Micalizio “A Biomimetic Polyketide-Inspired Approach to Small Molecule Ligand Discovery” Nature Chem. 2012, 4, 99-104.

M. A. Tarselli, K. M. Raehal, A. K. Brasher, C. Groer, M. D. Cameron, L. M. Bohn, G. C. Micalizio, “Synthesis of Conolidine, a Potent Non-Opioid Analgesic for Tonic and Persistent Pain” Nature Chem. 2011, 3, 449-453.

D. Yang, G. C. Micalizio, “Convergent and Stereodivergent Synthesis of Complex 1-Aza-7-Oxabicyclo[2.2.1]heptanes” J. Am. Chem. Soc. 2011, 133, 9216-9219.

V. Jeso, L. Cherry, T. K. Macklin, S. C. Pan, P. V. LoGrasso, G. C. Micalizio “Convergent Synthesis and Discovery of a Natural Product-Inspired Paralog-Selective Hsp90 Inhibitor” Org. Lett. 2011, 13, 5108-5111.

D. P. Canterbury, G. C. Micalizio, “Convergent Route to the CDEF Tetracycle of Pectenotoxin-2” Org. Lett. 2011, 13, 2384-2387.

V. Jeso, G. C. Micalizio, "Total Synthesis of Lehualide B by Allylic Alcohol–Alkyne Reductive Cross-Coupling" J. Am. Chem. Soc. 2010, 132, 11422-11424.

P. S. Diez, G. C. Micalizio, "Chemoselective Reductive Cross-Coupling of 1,5-Diene-3-ols with Alkynes: A Facile Entry to Stereodefined Skipped Trienes" J. Am. Chem. Soc. 2010, 132, 9576-9578.

T. K. Macklin, G. C. Micalizio, "Convergent and Stereospecific Synthesis of Skipped Polyenes and Polyunsaturated Fatty Acids" Nature Chem. 2010, 2, 638-643.

M. Z. Chen, M. McLaughlin, M. Takahashi, M. A. Tarselli, D. Yang, S. Umemura, G. C. Micalizio "Preparation of Stereodefined Homoallylic Amines from the Reductive Cross-Coupling of Allylic Alcohols with Imines" J. Org. Chem. 2010, 75, 8048-8059.

T. K. Macklin, G. C. Micalizio, "Total Synthesis and Structure Elucidation of (+)-Phorbasin C" J. Am. Chem. Soc. 2009, 131, 1392-1393.

D. Yang, G. C. Micalizio, "A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-Hydroxymethyl Substituted Allylic Silanes with Imines" J. Am. Chem. Soc. 2009, 131, 17548-17549.

J. K. Belardi, G. C. Micalizio, "Conversion of Allylic Alcohols to Stereodefined Trisubstituted Alkenes: A Complimentary Process to the Claisen Rearrangement" J. Am. Chem. Soc. 2008, 130, 16870-16872.

H. A. Reichard, J. C. Rieger, G. C. Micalizio Total Synthesis of Callystatin A by Titanium-mediated Reductive Alkyne–Alkyne Cross-Coupling Angew. Chem. Int. Ed. 2008, 47, 7837-7840.

J. K. Belardi, G. C. Micalizio Total Synthesis of Macbecin I Angew. Chem. Int. Ed. 2008, 47, 4069-4072.

M. Takahashi, G. C. Micalizio Regio- and Stereoselective Cross Coupling of Substituted Olefins and Imines. A Convergent Stereoselective Synthesis of Saturated 1,5-Aminoalcohols and Substituted Piperidines. J. Am. Chem. Soc. 2007, 129, 7514-7516.

F. Kolundzic, G. C. Micalizio Synthesis of Substituted 1,4-Dienes by Direct Alkylation of Allylic Alcohols. J. Am. Chem. Soc. 2007, 129, 15112-15113.