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The purpose of this exercise is to take what you have learned to the next level, and bring together the many reactions that you have learned to build creative synthetic strategies. An equally important goal is to develop the skills of creative cooperation in this endeavor. Organic chemists seldom work alone, but rather consult with each other to determine what weaknesses a plan may have before setting out on a multi step synthesis, and to determine alternative synthetic strategies in case a planned step does not provide the expected product. There are a few rules that we need to follow in order to maintain a high standard and to give each class member the best opportunity to make contributions. These are: 1) A maximum of 3 people can sign up for any one molecule 2) Between now and November 15th, you may sign up for only one molecule. This gives all class members a chance to take part in this project. If you have ideas about another molecule, you may message the people that are working on that mlecule to share your ideas, but please refrain from posting synthetic schemes on another molecule to give them a chance to figure it out. 3) After November 15th, you can sign up for any molecule that is still available. Any work that you do counts for extra credit up to a maximum of 100 points. 4) If you do not post anything on the prolem within 1 week of signing up for it, your name may be taken off of the list, and another person's put up. Post early, and post often. Your work on this wiki is not a finished product, but a work in progress until the end of the term 5) A complete project that recieves full credit should consist of the following: A) at least one retrosynthetic analysis (disconnection) (see Wade, pages 372 through 374) B) a reaction scheme showing each of the synthetic steps with starting materials, products, reagents and conditions C) a paragraph or so describing the logic of a synthetic strategy and why it would be the most likely to give the desired product. D) References to any sources that were used. These should include the journal title, volume, issue, year and page number, the book title, auther, publisher, and page number, or the website title, URL and author.  6) All reactions that are proposed should be accompanied by a page reference to a book journal article or web page (with web pages pay attention to papers referenced in that page. If there are none, be suspicious of the information there.) The reference should contain sufficient information for a reader to find the exact page of that book or journal article where that reaction can be found. 7) At least one reference should be to a source other than Wade. 8) Carbon limits on starting materials do not apply to reagents that do not contribute carbon atoms to the target molecule, for example, triphenyl phosphene or Sia-Borane can be used even if the carbon limit is two or six.
 * It is not sufficient to just cut and paste a reaction sequence from a journal without really understanding what is going on in the synthesis. **

These are all the rules. My suggestion is to post frequently and create a lively dialogue on the synthetic strategy. Design of an organic synthesis, like any other creative endeavor, does not happen in a single step, but is rather a process of thinking, writing, rethinking, and rewriting. You will be graded, not on whether you come up with the perfect synthesis in one try, but rather on the quantity and quality of your contributions. You can always respond and re-work your strategy according to the suggestions of others. I will comment on the proposed synthesese as much as possible, to give you a chance to work out the bugs. For this reason it is important to post early and often, not to wait until the last minute Remember that there is more than one correct synthesis, just as there are many incorrect ones. In evaluating alternatives, take into account that the best synthesis 1) minimizes the number of steps, 2) has reactions that yield predominantly the desired product, with a minimum of side products, 3) subsequent reactions do not affect the desired functional groups placed by previous reactions (i.e. the most labile functional groups are placed last). When you see something that you would like to work on, Click "edit" in upper right. Put your name down, and click "Save". Then click the blue link in the bottom of that text section. This will take you to the page of that molecule. You can also click the link from the home page. You make changes in the molecule page the same way.  To insert pictures you first need to upload them from your computer. Do this by clicking on the picture above, beside the TV set. Then click on the upload tab.  It is best to get together as a group and divide the work. Make a note of who did what on the molecule page. Good luck :-)

**Great website that allows you to find reactions by specifying the product and the reactant:** WebReactions Another good source of reactions is this website [|organic synthesis website] here is the hyperlink for[| chemsketch]
 * Chemsketch download**

smjp1 signup 1) Alfred Rush

2)Katalin Sagi

3) Olatubosun O. Ojekunle

smjp2

Sign up 1)

2)

3

These two amazing looking molecules were designed by [|Seth Marder] and is colleague [|Joseph Perry] at Georgia Tech. to absorb intensly focused blasts of ifrared laser light through a process called non linear optics, or two photon absorption. This technique allows them to build amazingly complex 3 diminsional structures on a micron scale. Components built this way may someday be used in micro-robots. It is described more fully in this [|news story] from the Georgia tech paper. I will call these SMJP1 and SMJP2, respectively, because the IUPAC names would be way too long. Here are a couple of examples of micro-3D structures:



melphalan Sign up1) Jenny Saravia I moved the picture to the melphalan page see the hyperlink above Bruce Bondurant 2) Miranda Maestrelli

3)Astrid Sandoval

4)Nikita Green

Melphalan is a cousin of the deadly mustard blister gasses used by the late dictator Saddam Hussein against Kurdish villages and Iranian troops. This compound, rather than taking lives, is being developed as an anticancer drug to save lives. It works by adding to the DNA of rapidly dividing cells. You can use any readily available starting material containing 6 or fewer carbon atoms.

pyrene lipid

Sign up 1)

2)

3

This synthetic amphiphile (lipid) molecule would line up side by side and hydrophobic tail to hydrophobic tail to form sheets much like a cell membrane. The dimercaptosuccinate group is a well known mercury chelator. Membranes containing this lipid would probably serve as mercury detectors because of the change in the fluorescence of the pyrene in the lipid tail that would occur when the thiols grab onto a mercury ion. Look at this molecule as three pieces attached to a glycerol, and do your disconnection with that in mind. Consider taking advantage of the regiospecificity of nucleophilic substitution on a protected 2.3-epoxypropan-1-ol. You can use any compound that is available in the Sigma Aldrich chemical catalog as a starting material. []

sertraline



Sign up 1) Meaghan Bartlett

2)Kerri Brinegar

3) James Mateka

Who says oganic chemistry is depressing? This is Sertraline, the active ingredient in Zoloft anti depressant. Devise a synthesis of a the racemic mixture of this compound containing only these two stereoisomers. Use any readily available starting material that has 6 carbons or less. See [] for what is readily available.

monomers Sign up 1) JOHNNY VELASQUEZ (Extra Credit)

2) James Mateka (Extra Credit)

3)

4)

These are two monomers that I dreamed up as a way to create sticky polymers. The monomer on the left should, when co-polymerized with acrylamide, make a polymer that is a poly-dien. The monomer on the right, when co-polymerized with a diol, such as hydrolyzed PETE, should make a poly-dienophile. Designing a synthesis for these compounds should be a good exercise in aromatic substitution reactions, the hofmann rearrangement and maybe even diels alder reactions on benzynes. I recommend that two people work on the N-(3-(furan-2-yl)propyl) acrylamide, and that two people work on the 5,7-diisocyanatonaphthalene-1,4-dione. In each case, any readily available compound containing 6 carbons or less is an acceptable starting material.

thyroxine

Sign up 1) Jeffrey Dujuste

2)Alain Diaz

3.)

This is a hormone that is used to treat thyroid diseas. In this synthesis, consider what functional groups or protecting groups you can use to get this type of substitution pattern around the ring. You can use any readily available starting material containing 6 or fewer carbon atoms.

atropine Sign up 1)Alain Diaz

2)Katalin Sagi (extra credit)

3) Merin Thomas

4) Saleel Velankar (extra credit)

Atropine a natural product that is effective against poisoning by a class of chemical warefare agents known as acetocholineesterase inhibitors. It is also an effective against many types of insectoside poisoning.A key step in this synthesis is the famous Tropinone synthesis, published by Robert Robinson in 1917. You can use any readily available starting material containing 6 or fewer carbon atoms.

tropinone synthesis

Sign up 1)Andradeen T Brown 2)Nadine Foxworth

3 James Mateka 4.) Merin Thomas (extra credit)

Here is a more open ended project: Do some research in chemistry journals and books, and find a natural product synthesis other than atropine, that uses Robinson's famous tropinone synthesis, shown above. Present the synthesis in the wiki.

caged fluorescein

Sign up1)Astrid Sandoval

2)Nikita Green

3Jenny Saravia

This complicated looking molecule is acturally quite easy to synthesize. It is colorless, but turns into highly fluorescent fluorescein when it is exposed to 330nm light from a nitrogen laser. Use any starting materials that contain 8 carbons or less.

prazosin

ign up 1)Elein Ravelo

2)Lydia Owusu

3) jeffrey Asphall/ Jeffrey Dujuste

Sweet Dreams! Prazosine is a blood pressure medicine that shows promise as a drug that will prevent the nighmares that many veterans returning from Iraq and Afganistan with PTSD are suffering from. Make this compound from any monocyclic or acyclic starting materials that are available from the [|sigma aldrich catalog]

Resveratrol

Resveratrol
Sign up 1)Amber Rosa

2)Gloria Tucker

3) Saleel Velankar

4) Meaghan Bartlett (extra credit) This terpine from red wine is a potential fountain of youth molecule that has been shown to slow the aging process in laboratory animals. It may play a role in the  so called "French Paradox". Figure out a practical synthesis for this compound,  and you can print money.  You can use any readily available starting material containing 6 or fewer carbon atoms.

Kinoprene

Sign up 1) Johnny Velasquez

2) Carlos Avila

3) Elein Ravelo

Kinoprene is an insect hormone. Derivatives of this type of compound have the potential of being highly selective, and non toxic (to us and non target animals) insectisides. Research in this area may bring about a new "green revolution", Make this molecule from any starting materials that are readily available from the [|sigma aldrich catalog]