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Eberly College of Science Department of Chemistry
Steven M. Weinreb

Steven M. Weinreb

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  • Russell and Mildred Marker Professor of Natural Products Chemistry
Office:
537 Chemistry Building
University Park, PA 16802
Email:
(814) 863-0189

Education:

  1. A.B., Cornell University, 1963
  2. Ph.D., University of Rochester, 1967

Selected Publications:

Chauhan, P. S.; Weinreb, S. M.  Convergent Approach to the Tetracyclic Core of the Apparicine Class of Indole Alkaloids via a Key Intermolecular Nitrosoalkene Conjugate Addition.  J. Org. Chem. 2014, 79, 6389.

Feng, Y.; Majireck, M. M.; Weinreb, S. M.  Total Syntheses of the Monoterpene Indole Alkaloids (±)-Alstilobanine A and E, and (±)-Angustilodine.  J. Org. Chem. 2014, 79, 7 (Featured Article).

Sengupta, R.; Weinreb, S. M.  A One-Pot Umpolung Method for Preparation of a-Aryl Nitriles from a-Chloroaldoximes via Organocuprate Additions to Transient Nitrosoalkenes.  Synthesis 2012, 44, 2933.

Feng, Y.; Majireck, M. M.; Weinreb, S. M.  Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)-Alstilobanine A.  Angew. Chem. Int. Ed. 2012, 51, 12846.

Sacher, J. R.; Weinreb, S. M.  Construction of the Azocane (Azacyclooctane) Moiety of the Lycopodium Alkaloid Lycopladine H via an Intramolecular Hydroaminomethylation Strategy.  Org. Lett. 2012, 14, 2172.

Chauhan, P. S.; Majireck, M. M.; Weinreb, S. M.  Regioselective a-Monochlorination of N-Protected-3 piperidones.  Heterocycles 2012, 84, 577.

Sacher, J. R.; Weinreb, S. M.  Discussion Addendum for 2-Trimethylsilylethanesulfonyl Chloride (SES-Cl).  Org. Synth. 2012, 89, 34.

Sengupta, R.; Witek, J. A.; Weinreb, S. M.  Stereochemical Investigations of Conjugate Additions of Carbon- and Heteronucleophiles to Ring-Substituted Nitrosocyclohexenes.  Tetrahedron 2011, 67, 8229.

Sacher, J. R.; Weinreb, S. M.  Exploratory Studies Towards a Total Synthesis of the Unusual Bridged Tetracyclic Lycopodium Alkaloid Lycopladine H.  Tetrahedron 2011, 67, 10203.

Witek, J. A.; Weinreb, S. M.  Investigation of the Stereochemistry of Intermolecular Conjugate Additions of Nucleophiles to Acyclic Nitrosoalkenes.  Org. Lett. 2011, 13, 1258.

Kumar, P.; Li, P.; Korboukh, I.; Wang, T. L.; Yennawar, H.; Weinreb, S. M.  Further Studies of Intramolecular Michael Reactions of Nitrosoalkenes for Construction of Functionalized Bridged Ring Systems.  J. Org. Chem. 2011, 76, 2094.

Majireck, M. M.; Witek, J. A.; Weinreb, S. M.  An Expedient Reductive Method for Conversion of Ketoximes to the Corresponding Carbonyl Compounds.  Tetrahedron Lett2010, 51, 3555.

Liu, P.; Seo, J. H.; Weinreb, S. M.  Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (±)-Communesin F.  J. Org. Chem. 2010, 75, 2667.

Li, P.; Majireck, M. M.; Witek, J. A.; Weinreb, S. M.  Efficient Methodology for Alkylation of Vinylnitroso Compounds with Carbon Nucleophiles.  Tetrahedron Lett. 2010, 51, 2032.

Liu, P.; Seo, J. H.; Weinreb, S. M.  A New Total Synthesis of the Polycyclic Fungal Metabolite (±)-Communesin F.  Angew. Chem. Int. Ed. 2010, 49, 2000.

Information:

Synthesis of natural products; development of new synthetic methods; heterocyclic chemistry; pericyclic reactions and cycloadditions.

Total Synthesis of Heterocyclic Natural Products

Professor Weinreb's research group is currently involved in the total synthesis of a number of complex heterocyclic natural products with significant pharmacological activity. Throughout all of these projects, heavy emphasis is being placed on developing and exploiting new synthetic methodology of potentially wide application in organic chemistry. For example, the unusual polycyclic marine natural product sarain A will be synthesized from the tricyclic intermediate in Figure 1. This compound has been prepared via the key allylsilane-N-sulfonyliminium ion cyclization shown in the figure. In addition, work is presently in progress on total synthesis of the biogenetically related anticancer marine alkaloid madangamine A.

A novel method for amide oxidation has been developed using the free radical sequence shown in Figure 2. This process provides a simple, convenient access to N-acylimines, which are widely useful synthetic intermediates. This chemistry is now being applied in an approach to total synthesis of the marine sponge anticancer alkaloid fasicularin.

A new type of pericyclic ene reaction of allenylsilane imines and related compounds has recently been discovered (Figure 3). This methodology provides a stereospecific route to diverse functionalized nitrogen-containing ring systems. The chemistry is currently being utilized in enantioselective total syntheses of the poison frog neurotoxin (-)-gephyrotoxin and the indole alkaloid (-)-ibogamine.

Several other complex marine natural products are also presently targets for total synthesis. Included in this group is the unique hepatotoxin cylindro-spermopsin produced by a fresh water blue-green alga. The key steps in this synthesis utilize methodolgy previously developed in the Weinreb group. The approach involves the intramolecular N-sulfinylurea [4+2]-cycloaddition shown in Figure 4, followed by a stereospecific ring opening-allylic sulfoxide [2,3]-sigmatropic rearrangement.

Research Interests:

Organic

Total Synthesis of Natural Products

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