Bioorganic/Organic

The Lewis Group is engaged in the synthesis of complex natural products and the design of new catalysts to enable new bond disconnections in organic chemistry.

Research The synthesis of complex natural products and the discovery of methods enabling access to such molecules remain at the forefront of synthetic organic chemistry. Nature provides an endless array of complexity and bioactivity that inspires chemists to develop new strategies to meet these challenges. Research in the Lewis laboratory will encompass a broad spectrum of topics that include total synthesis of rare natural products, method development for new bond disconnections and emulation of Nature's enzymes and reactivity.

Moschitto, M.J., Anthony, D.R., Lewis, C.A. “Syntheses of Arnottin I and Arnottin II.” J. Org. Chem. 2015, ASAP. DOI: 10.1021/acs.joc.5b00107

Moschitto, M.J., Vaccarello, D.N., Lewis, C.A, “Regiodivergent Addition of Phenols to Allylic Oxides: Control of 1,2 and 1,4-Additions for Cyclitol Synthesis.” Angew. Cheem Int. Ed.. 2015, 54, 2142 –2145. DOI: 10.1002/anie.201410228

T. Newhouse, C. A. Lewis, K. J. Eastman, P. S. Baran Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole-Aniline Coupling: Psychotrimine and Kapakahines B and F J. Am. Chem. Soc. 2010, 132, 7119-7137.

I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, P. S. Baran Total Synthesis of Palau’amine Angew. Chem. Int. Ed. 2010, 49, 1095-1098. Angew. Chem. 2010, 122, 1113-1116.

A. W. Schultz, C. A. Lewis, M. R. Luzung, P. S. Baran, B. S. Moore Functional Characterization of the Cyclomarin/Cyclomarazine Prenyltransferase CymD Directs the Biosynthesis of Unnatural Cyclic Peptides J. Nat. Prod. 2009, 72, 373-377.

M. R. Luzung, C. A. Lewis, P. S. Baran Direct, Chemoselective N-tert-Prenylation of Indoles by C-H Functionalization Angew. Chem. Int. Ed. 2009, 48, 7025-7029. Angew. Chem. 2009, 121, 7159-7163.

T. Newhouse, C. A. Lewis, P. S. Baran Enantiospecific Total Syntheses of Kapakahines B and F J. Am. Chem. Soc. 2009, 131, 6360-6361.

C. A. Lewis, K. E. Longcore, S. J. Miller, P. A. Wender An Approach to the Site-Selective Diversification of Apoptolidin A with Peptide-Based Catalysts J. Nat. Prod. 2009, 72, 1864-1869.

C. A. Lewis, J. Merkel, S. J. Miller Catalytic Site-selective Synthesis and Evaluation of a Series of Erythromycin Analogs Bioorg. Med. Chem. Lett. 2008, 18, 6007-6011.

C. A. Lewis, J. L. Gustafson, A. Chiu, J. Balsells, D. Pollard, J. Murry, R. A. Reamer, K. B. Hansen, S. J. Miller A Case of Remote Asymmetric Induction in the Peptide-Catalyzed Desymmetrization of a Bis

ol) J. Am. Chem. Soc. 2008, 130, 16358-16365.

C. A. Lewis, A. Chiu, M. Kubryk, J. Balsells, D. Pollard, C. K. Esser, J. Murry, R. A. Reamer, K. B. Hansen, S. J. Miller Remote Desymmetrization at Near-Nanometer Group Separation Catalyzed by a Miniturized Enzyme Mimic J. Am. Chem. Soc. 2006, 128, 16454-16455. Also see “Research Highlights” Nature, 2006, 444, 974-975.

C. A. Lewis, S. J. Miller Site-selective Derivatization and Remodeling of Erythromycin A by Using Simple Peptide-Based Chiral Catalysts Angew. Chem. Int. Ed. 2006, 45, 5616-5619. Angew. Chem. 2006, 118, 5744-5747. Also see “Editor’s Choice” Science, 2006, 313, 592-593.

C. A. Lewis, B. R. Sculimbrene, Y. Xu, S. J. Miller. Desymmetrization of Glycerol Derivatives with Peptide-Based Acylation Catalysts Org. Lett. 2005, 7, 3021-3023.

C. A. Lewis, R. R. Tykwinski. Chiral, Cross-conjugated Isopolydiacetylenes Chem. Comm. 2006, 34, 3625-3627.

C. A. Lewis, M. Wang, A. Mar. Vanadium Nickel Antimonide, VNi0.26

Sb Acta Cryst. 2002, E58, i39-i40.