(+) – Crocacin C

Chakraborty TK, Jayaprakash S, Laxman P. Total synthesis of (+)-crocacin C. Tetrahedron 2001;57(46):9461-9467.

http://www.sciencedirect.com/science/article/B6THR-44C8T5Y-F/1/1bda2a711363a1360e9974d68e11a6fd

Reviewed by: Erin E. Albers, Timothy P. De Chant, and Abby M. Sprenger

(+) – crocacin C

The natural source of the compound (+) – crocacin C is Chrondromyces crocatus. Chrondromyces crocatus is a type of bacteria which acts as a fungus, it comes from a species of Myxobacteriales. (+) – crocacin C is of interest to makers of medicine because it can be used as a antifungal or cytotoxic agent. The antifungal part applies to any sort of fungus, be it athletes foot, or what have you. (+) – crocacin C is also a cytotoxic agent. By Webster’s definition a cytotoxic agent is one “that harms or destroys living cells (cytotoxic drug therapy), or relating to cytotoxins, their effects.” (Webster’s Dictionary). A cytotoxin is, therefore, “ a chemical substance that destroys, or impairs the function of, specific living cells.” This would be very useful in the treatment of many forms of cancer because it only destroys specific cells. If it was possible for the cytotoxins to attack the cancer cells we might be on our way to finding the cure for cancer. This could also be a reason why we only need one diastereomer of the molecule, for if we had more then one the resulting effect could either be a cancellation of the desired effect or a potentially harmful one.

The purpose of the Sharpless asymmetric epoxidation ensured both the formation of the desired epoxy alcohol and a high yield of that desired compound (93% in this case). The high yield in this case was extremely advantageous, saving the chemist both time and money by making the most of the available compounds. By almost guaranteeing a diastereometrically pure sample, the chemists were better prepared for the next step of their reaction, the regioselective opening of the epoxide.

For this project Erin drew all of the molecules, looked up information and helped to look for an article. Timothy worked on the discussion of the retrosynthesis and revising the paper. Abby found the article, did some research, and typed the paper.