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Sunday, 14 December 2014

One day One Scientist Honoured........Professor Robert B.Grossman 15 DEC 2014



Bob Grossman's pictureRobert B. Grossman

Professor of Chemistry
Synthetic Organic Chemistry

 

 

 


Robert B. Grossman
Professor of Chemistry (Organic Chemistry)
Synthesis of Biologically Relevant Organic Compounds

 

 https://www.as.uky.edu/map-directions

 The University of Kentucky's College of Arts and Sciences is located in Kentucky's scenic Bluegrass region, only a few minutes from downtown Lexington. The college is housed in 21 buildings and is home to more than 5,800 undergraduate and graduate students and over 500 faculty and staff
College of Arts & Sciences
202 Patterson Office Tower
Lexington, KY 40506-0027
Phone: 859-257-8354

In collaboration with the Atwood group, we are preparing a series of simple S containing compounds to coordinate to Hg and to precipitate it from solution. An REU student would prepare such a compound and see how effective it is as a Hg precipitator.
I have found that undergraduates learn the most when they can begin with a known synthetic sequence and then follow it up with novel reactions. They gain
experience and confidence when they prepare a known compound and can compare their results with those reported in the literature. They then experience the joys and frustrations of research at the frontiers of knowledge when they carry out reactions whose outcomes are less certain, and they have to identify both conditions that lead to single products and the identities of those products. For these reasons, the project I have described above is perfect for an REU experience.
Further details of Dr. Grossman's work are given on the Chemistry website.

 

Office: 339 Chemistry-Physics Building
Phone: (859) 257-1285
FAX: (859) 323-1069
Email: robert.grossman@uky.edu

1987 A.B., Princeton University
     Advisor: Robert A. Pascal, Jr.
1992 Ph.D., Massachusetts Institute of Technology
     Advisor: Stephen L. Buchwald
1992-1994 NATO-NSF Post-doctoral Fellow, Cambridge University
     Advisor: Steven V. Ley

Postdoctoral Fellowships available for qualified applicants (US citizens only).



The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd edition.

New! Web-based, interactive mechanism problems from the textbook!
I teach a two-day "short course" based on this book that is intended for BS- and MS-level chemists in the pharmaceutical and contract synthesis industries. Please contact me if you are interested in bringing me to your company's site to teach the course.

Our group develops new synthetic methods and applies them to the synthesis of natural products and biologically relevant compounds. Students learn skills that prepare them for employment in the pharmaceutical and contract synthesis industries.

 

Research Project 1: Double Annulation

Our group has discovered a suite of reactions we call the double annulation route to fused bicyclic compounds. In the first step of the double annulation, two good carbon acids connected by a tether and an ethynyl ketone undergo a double Michael reaction to give a carbocyclic or heterocyclic compound in what is formally an [n + 1] annulation.

our double Michael reaction
The functionality in the double Michael adducts can be used to create a second (and sometimes even a third) carbocyclic or azacyclic ring in a second step. Bicyclic ring systems that can be produced include trans-decalins, trans-hydrindanes, trans- and cis-perhydroisoquinolines, trans- and cis-perhydro-2-pyrindines, trans-perhydroindoles, trans-perhydropyrrolo[3,2-c]pyridines, cis-perhydro[1,7]naphthyridines, and tricyclic N,N'-diacylaminals. The latter self-assemble in the solid state into "supramolecular chair cyclohexanes".
double annulation products
The utility of the double annulation for natural product synthesis is established by a very short, stereoselective synthesis of the putative structure of sacacarin, a clerodane diterpenoid. Our synthesis proves that the group that discovered this compound incorrectly determined the location of the bridging lactone carbonyl group. We have proposed a revised structure for sacacarin and have proved its correctness by synthesizing this compound from the putative sacacarin.
Total synthesis of putative and actual sacacarin.
Current efforts are aimed at further expanding the scope of the double annulation reaction and applying it to the total synthesis of natural and unnatural products. We are now developing total syntheses of the biologically active alkaloids yohimbine, an α2-adrenergic receptor antagonist, and codeine, a representative of the morphine family.
Some natural products accessible by double annulation.

 

 

Research Project 2: Polycyclic, Polyprenylated Acylphloroglucinols

We have recently begun a new program aimed at the synthesis of the polycyclic, polyprenylated acylphloroglucinols (PPAPs), a large group of natural products with fascinating chemical structures and biological activities. For example, hyperforin is thought to be the bioactive constituent in St. John's wort, an herbal remedy for depression. Garsubellin A has properties that make it a potential lead in the search for drugs to treat Alzheimer's disease. Xanthochymol prevents microtubule depolymerization, a property it shares with the anticancer drug Taxol. We are exploring both biomimetic and nonbiomimetic routes to these and other PPAPs.
some PPAPs

 

 

 

Research Project 3: Loline Biosynthesis

We are elucidating the biosynthetic route to loline, a naturally occurring insecticide that is produced by fungi that live between the cell walls of certain grasses. Our role is to synthesize isotopically labelled putative biosynthetic intermediates. These compounds are fed to the fungi, and the loline that they produce is isolated and checked for isotopic enrichment. This project is being carried out in collaboration with Profs. Chris Schardl and Lowell Bush in the College of Agriculture. We are also exploring new total synthetic routes to loline.
structure of loline

 

Education Project: Web-Based Interactive Organic Chemistry Homework

In collaboration with Prof. Raphael A. Finkel of the Department of Computer Science, we have developed a Web-based interactive organic chemistry homework program, ACE Organic. In the typical organic chemistry course, students are assigned questions out of a textbook for which a solutions manual is available. Students struggle with a question for a few minutes, look up the answer, and then feel as if they understand how to answer the question themselves. A computer program that can tell students that their responses are incorrect without giving away the correct answer is likely to be a more effective teaching tool.
Many Web-based chemistry homework programs already exist, but ACE Organic has features that, to our knowledge, are not present in combination in any other homework program:
  1. ACE Organic permits students to draw structural responses to posed questions with a graphical interface. ACE questions are typically draw-the-product, spectroscopy, and nomenclature problems. We are working on extending this capability to mechanism and conformation problems. Most other Web-based homework programs require text-based, numeric, or multiple-guess responses, none of which are well-suited to organic chemistry, where responses are usually structural drawings.
  2. ACE Organic offers response-specific feedback to students who submit incorrect responses. The feedback that ACE provides depends on the structural characteristics of the response. The feedback corrects errors in the students' reasoning and guides them gently to the correct answers.
  3. ACE Organic permits instructors to add to or modify the question database. An instructor may want to add material not covered by the questions in the database, or an instructor might want to correct an error in a question or modify it to offer better feedback for incorrect responses.
Prentice-Hall is now marketing ACE Organic world-wide. Students who buy a new Prentice-Hall textbook receive access to ACE for only an additional $5; others may purchase access to ACE at $25–30. Contact your Prentice-Hall representative to obtain access to ACE.

Funding:

We are grateful to the following organizations for funding our research:
The National Science Foundation and The National Institutes of Health and Prentice-Hall, Inc.


Publication list.

Graduate studies in the UK Department of Chemistry.

Other useful and interesting chemistry-related sites:

  • Word processing and HTML:
  • Some Java software for chemistry:
    • IUPAC's online naming service.
    • Jmol, an open-source, platform-independent Java software for viewing chemical structures in 3D. It is intended as a substitute for Chime, which does not work with MacOS X browsers. Copy a URL of a MOL or PDB file from a Web site and paste it (use CONTROL-V, not COMMAND-V) directly into Jmol to see and manipulate the structure.
    • Marvin, programs for drawing, manipulating, and viewing chemical structures. Free for student and academic use! Both PC and Mac desktop versions available, as well as Java applets for building Web applications.
    • A more accurate vapor-pressure nomograph.
    • Our own functional-group finder. Find out what functional groups are in your compound, and then see how each functional group is defined.
    • Our own electron-flow arrows calculator. Draw starting materials and electron-flow (curved, Robinson, mechanism) arrows, and the program will calculate the products. Especially useful for students trying to learn how to draw electron-flow arrows properly.
  • Spectroscopy:
    • The Spectral Database System of the Japanese National Institute of Advanced Industrial Science and Technology has 1H and 13C NMR, IR, mass, and Raman spectra for a large number of compounds.
    • NMRShiftDB is an open-source, open-access, open-submission, open-content web database for chemical structures and their associated nuclear magnetic resonance data.
    • The chemistry Webbook of the US National Institute of Standards and Technology doesn't have NMR data but has a lot of other information.
    • iNMR, NMR spectral simulation software for Mac OS X.
    • A paper tabulating chemical shifts of common impurities in NMR spectra.
    • Tables and more tables of 1H and 13C NMR chemical shifts.
  • Chemistry community:
  • Miscellaneous chemistry references:

 

 

 

Personal:

The University funds lucrative postdoctoral fellowships for women and for members of ethnic groups underrepresented in the sciences (US citizens only). If you are interested in working in our group and you qualify for either of these fellowships, I would be delighted to sponsor your application. Please contact me for more information.



















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