Author(s): Brigham Warner, Chloe Adams
Mentor(s): Barry Lloyd
Institution Weber
Norborn-2-en-7-one and norborn-2-en-anti-7-ol are synthetic precursors used to make larger model compounds and investigate their possible structure/reactivity relationships. Norborn-2-en-7-one is an important base that is used to synthesize pharmaceutical drugs and is currently being researched for anti-tumor therapy. Aside from the pharmaceutical aspect of this interesting molecule, its derivatives have interesting qualities that warrant further study. The current synthetic route for norborn-2-en-7-one involves highly toxic, expensive, poly-chlorinated substances, flammable ethene gas, and large amounts of dangerous sodium metal in the dechlorination step. We deemed it reasonable to construct a new synthetic route. We were unable to duplicate a literature synthesis of 1,1-diethoxycyclopentadiene to which (E)-1,2-bis(phenylsulfony)ethene would have been added as a dienophile. Attempts to add (E)-1,2-bis(phenylsulfonyl)ethene 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene were unsuccessful. A two step literature synthesis was discovered for making syn-nornorn-2-en-7-ol by which we have made some product. An attempt to convert the syn-7-alcohol to the anti-7-chloride with triphenylphosphine and carbon tetrachloride was unsuccessful so far. This chlorinated product can then be solvolyzed in water to form anti-norborn-2-en-7-ol. The syn-7-alcohol might be oxidized into the target norbornenone. The oxidation mechanism was tested on D-carvone in order to see if the alkene bonding was effected. While this reaction is currently being evaluated to see if it is viable to test on our syn alcohol products, we have been working on purifying our product as much as possible. A byproduct of the reaction to synthesize the syn product is t-butanol, which has proven to be difficult to remove. We hope to have proven results in the near future.