 |
| Born Rajkot, India, 1958. |
| University of Connecticut, B.S., 1980. |
| University of Pennsylvania, Ph.D., 1986. |
| Columbia University, Postdoctoral Fellow, 1986-1988. |
| The Ohio State University, Assistant Professor, 1988-1994; Associate Professor, 1994-1995. |
| The University of Chicago, Professor, 1995-. |
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| Accolades |
Editorial
Advisory Board Member, Journal of Organic Chemistry, 2004-2007. |
| Fellow of the American Association for the
Advancement of Science, 2004. |
| National Institutes of Health -
Medicinal Chemistry Study Section Member
1997, 1999-2003. |
| American Chemical Society Arthur
C. Cope Scholar Award, 2003. |
| Pfizer Research Award for Synthetic Organic Chemistry, 1995-98. |
| Merck Young Investigator Award,
1995. |
| Eli Lilly Granteeship, 1993-94. |
| American Cyanamid Faculty Award,
1994. |
| American Cancer Society Junior
Faculty Research Award, 1990-93. |
| DuPont Young Faculty Award, 1988-89. |
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| Viresh H. Rawal |
| Professor |
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| Research Interests: |
| Chemistry is, ultimately, about chemical reactions-developing them, understanding them, and using them to make interesting, useful molecules. Much of the activity in my research group is aimed at discovering new ways to make complex molecules, including the design of unique strategies to certain families of natural products and the development of broadly effective methods for chemical synthesis. |
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| The targets for our synthesis studies are selected for their intricate structures as well as their potent biological activities. We strive to devise routes that are concise, stereocontrolled, and high-yielding, and proceed through strategies that examine interesting aspects of structure and reactivity. Among the targets that we have successfully synthesized are: 5-oxo-silphiperfol-6-ene, (+)-tabersonine, geissoschizal, elisapterosin B, and strychnine. |
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| The targets that we are currently pursuing include the clinically important anticancer agent vinblastine, and the potent antiviral and anticancer agent mycalamide A. |
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| In recent years, a significant part of my group has focused on the development of effective catalysts for enantioselective reactions. The biologically important Aspidosperma family of alkaloids have provided the motivation for much of this work. We have found that salen-based chiral complexes catalyze the Diels-Alder reactions of amino-substituted dienes and a broad range of dienophiles, so as to produce the cycloadducts in high yields and excellent enantioselectivities. |
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| Significantly, we have discovered that TADDOL, a simple, commercially available chiral alcohol, functions as a catalyst for highly enantioselective cycloadditions. Reminiscent of enzymes and antibodies, hydrogen bonding to TADDOL provides both tremendous rate acceleration and exquisite selection for the formation of one enantiomer of the product. |
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| Selected References |
| Thadani, A. N.; Stankovic, A. R.;
Rawal, V. H. "Enantioselective Diels-Alder
Reactions Catalyzed by Hydrogen Bonding." P. N. A. S. 101, 5846-5850 (2004). |
| Waizumi, N.; Stankovic, A. R.;
Rawal, V. H. "A General Strategy
to Elisabethae Diterpenes:
Stereocontrolled Synthesis of
Elisapterosin B via Oxidative
Cyclization of an Elisabethin
Precursor." J. Am. Chem. Soc. 125, 13022-13023 (2003). |
| Huang, Y.; Unni, A. K.; Thadani,
A. N.; Rawal, V. H. "Hydrogen
Bonding by a Chiral Alcohol to an
Aldehyde Catalyzes Highly
Enantioselective Reactions." Nature 424, 146 (2003). |
| Huang, Y.; Rawal, V. H. "Hydrogen-
Bond-Promoted Hetero-Diels-Alder
Reactions of Unactivated Ketones." J. Am. Chem. Soc. 124, 9662-9663
(2002). |
| Huang, Y.; Iwama, T.; Rawal, V. H.
"Design and Development of
Highly Effective Lewis Acid
Catalysts for Enantioselective Diels-
Alder Reactions." J. Am. Chem. Soc. 122, 5950-5951 (2002). |
| Kozmin, S. A.; Iwama, T.; Huang,
Y.; Rawal, V. H. "An efficient
approach to Aspidosperma
alkaloids via [4+2] cycloadditions
of aminosiloxydienes:
Stereocontrolled total synthesis of
(+/-)-tabersonine. Gram-scale
catalytic asymmetric syntheses of
(+)-tabersonine and (+)-16-
methoxytabersonine. Asymmetric
syntheses of (+)-aspidospermidine
and (-)-quebrachamine." J. Am. Chem. Soc. 124, 4628-4641
(2002). |
| Reddy, T. J.; Rawal, V. H.
"Expeditious syntheses of (+/-)-5-
oxosilphiperfol-6-ene and (+/- )-
silphiperfol-6-ene." Org. Lett. 2, 2711-2712 (2000). |
| Huang, Y.; Iwama, T.; Rawal, V. H.
"Highly enantioselective Diels-
Alder reactions of 1-amino-3-
siloxy-dienes catalyzed by Cr(III)-
salen complexes." J. Am. Chem. Soc. 122, 7843-7844 (2000). |
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Organic Chemistry 