Organic Chemistry
The organic chemistry group emphasizes the synthesis of complex natural and unnatural molecules of biological significance with an emphasis on the development of new synthetic methodologies. Isolation of bioactive natural products and synthesis aimed at drug discovery and development and medicinal chemistry are other important areas of research. Newer areas of research are related to utilization of parallel and combinatorial synthesis methods in complex molecule synthesis. Many of these projects are conducted in conjunction with the Center for Methodology and Library Development at Boston University (CMLD-BU).
Associated Faculty
Warren P. Giering
Organometallic chemistry
We have developed a protocol (the Quantitiative Analysis of Ligand Effects,
QALE) that allows us to relate changes in the physicochemical properties
of inorganic and organometallic compounds to variations in the stereoelectronic
properties of ancillary or incipient phosphorus(III) ligands. We are
using QALE in the studies of asymmetric catalytic reactions in order
to tune the efficiency of the catalyst so that we can achieve high rate,
chemoselectivity, and stereoselectivity.
Guilford Jones
Synthesis of model electron transport systems
This research focuses on utilizing fluorescence properties of organic
dyes in a variety of applications that include the monitoring of conformational
changes and the concentrations of water soluble polymers. Other applications
include the development of unique luminescent marks that can be used
in covert marking of documents or products.
James Panek
Stereocontrolled synthesis of complex organic molecules
The Panek Laboratory focuses on the design and development of new methods for stereocontrolled synthesis of complex organic molecules. Once the scope of a methodology is determined, it is utilized in stereocontrolled synthesis of a natural product or a group of related natural product targets. These targets enable the preparation of chemical entities through diversity-oriented synthesis. The research goals are to enhance structural diversity available from Nature and to prepare molecules with novel chemical or biological properties. These studies are often carried out in conjunction with the CMLD-BU.
John Porco
Organic synthesis and combinatorial chemistry
Our research involves the development of new methodologies for chemical
synthesis and their application to synthesis of complex natural products
and similar molecules. Targets for synthesis include pharmacologically
active compounds where the preparation of structural variants will allow
us to dissect regulatory interactions with biomolecules, with the aim
of understanding the origin of their biological properties. In many instances,
we will attempt to redesign particular molecules and fine-tune their
molecular structure through the use of combinatorial or parallel synthesis
approaches. Parallel synthesis using simple reaction blocks and workstations
will also be used for efficient optimization of new chemical reactions
and key synthetic transformations. Equipment for these efforts are located
in the Boston University Center for Streamlined Synthesis
(CSS). Many of the Porco Group projects are conducted in conjunction with the CMLD-BU.
Scott Schaus
Chemical methodologies, natural product synthesis, and chemical genomics
The Schaus Group develops new chemical methodologies, synthesizes natural products and small molecules with interesting biological activities, and uses chemical genomics techniques to study the effects of compounds on cellular processes. They use chemical synthesis, functional genomics, and bioinformatics to gain understanding of the effects of antiproliferative compounds on cellular processes. Their research projects work synergistically toward the development of a new asymmetric methodology and its application to interesting natural products. They use and develop techniques in genomics and biology to understand how these compounds affect cellular processes. Their work in chemical methodology focuses on the development of direct asymmetric carbon-carbon bond-forming reactions. They have been studying the Morita-Baylis-Hillman (MBH) reaction, a long-standing challenge in asymmetric catalysis, concentrating on the phosphine-promoted reaction. They have successfully identified a highly enantioselective Brønsted-acid-catalyzed MBH reaction. The reaction not only addresses a gap in asymmetric synthetic methodology but also identified a unique example of chiral Brønsted acid catalysis. Future work will develop the reaction for use in synthesis, using it as a key step in the synthesis of the pycnanthuquinones, natural products with a unique mode of overcoming the symptoms of type 2 diabetes mellitus.
John Snyder
Organic synthesis and natural products
Our group focuses on synthetic organic chemistry and the isolation and
structure determination of biologically active natural products isolation.
Three main project themes describe the synthetic effort. The first is
inverse electron demand Diels-Alder chemistry in the synthesis of medicinally
important heterocycles and their structural analogues. The second is
development of the homo Diels-Alder reaction for the preparation of biologically
active terpenoids, and the third area of synthetic research is the preparation
of chiral anthracenes as templates for a Diels-Alder/retro Diels-Alder
sequence on polymer support of the preparation of synthetically important
synthons in parallel fashion.
Research in the Stephenson group is focused primarily upon the development of new strategies and methodologies for the synthesis of natural products. Of particular interest are the discovery of new asymmetric transformations and their application in the realm of complex molecule synthesis. We are taking a Target-Driven Approach to discovery in that we are drawing inspiration for new methodologies from the complex targets which are undertaken by students in the lab. Each graduate student is working on their own target molecule which incorporates a novel methodology into the synthetic plan.
Associated Graduate Courses
The following graduate courses in the specialization area of organic chemistry are offered:
GRS CH - 541 Natural Products Chemistry
Prereq: CAS CH 212 and consent of instructor. Chemical and biosynthetic pathways leading to important natural products derived from fatty acids, terpenes, amino acids, poluketides, shikimic acid, and other biosynthetic intermediates. Three hours lecture. Panek. 4 cr, 1st sem.
GRS CH 642 - Organic Reaction Mechanisms
Prereq: CAS CH 212, or consent of instructor. Fundamentals of organic reaction mechanisms; techniques used to study reaction mechanisms; reactive intermediates: carbonium ions, radicals, carbenes, nitrenes; acid/base catalysis, reactions for the carbonyl group, cycloaddition, nucleophilic displacement reactions, and redox chemistry. Three hours lecture. Porco. 4 cr, 1st sem.
GRS CH 643 - Synthetic Methods in Organic Chemistry
Prereq: GRS CH 641 and CH 642. Organic synthetic strategies for total synthesis. Various approaches for organic molecules whose synthesis constitutes major contributions to organic chemistry. Three hours lecture. Panek. 4 cr, 2nd sem.
GRS CH 644 - Medicinal Chemistry
Prereq: CAS CH 212 or equivalent and consent of instructor. Medicinal chemistry; synthetic organic chemistry and pharmacology as applied to development, testing, and production of medically useful agents. Lectures and discussions by research chemists affiliated with leading pharmaceutical companies. A research paper is required. Two hours lecture. 2 cr, 2nd sem.
GRS CH 741 - Organic Spectroscopy and Structure Determination
Prereq: GRS CH 641, CH 651, or equivalent. Spectroscopic methods in organic structure determination, with main emphasis on nuclear magnetic resonance. Snyder. 4 cr, either sem.
GRS CH 743 - Organometallic Chemistry
Prereq: GRS CH 631; recommended: CH 641, CH 642, and CH 643, or consent of instructor. Structure and bonding in transition metal organometallic compounds; descriptive chemistry of organometallic compounds; fundamental organometallic reaction mechanisms; important industrial catalytic processes; organometallic compounds in organic synthesis. Giering. 4 cr, either sem.
GRS CH 744 - Current Topics in Organic Chemistry
Prereq: GRS CH 641 and CH 642 or equivalent. Instructors cover topics related to their research. Topics include total synthesis, chiral synthetic methods, bio-organic chemistry, photochemistry, organic polymer chemistry, and natural products chemistry. Jones, Panek, Porco, Schaus, Snyder. 4 cr, either sem.