The summer of 1998 saw two students working in my lab on this project. Each tried to synthesize chiral nonracemic 3-phenylbenziodoxole acetate.
Steve Reitz, ’00 attempted to synthesize chiral non-racemic 2-iodobenzhydrol, an intermediate in the synthesis of the above compound, via an asymmetric reduction of 2-iodobenzophenone. Here are a couple of pictures of him doing a column. Steve worked for Pharmacia in Kalamazoo, MI, as an organic chemist in Drug Discovery for three years and then went to Medical School at Toledo, completed his residency in general and plastic Surgery and is practicing in the Columbus area.
Rachel Hector, ’00 chose to synthesize the same chiral compound as Steve using a chiral resolution of the racemic 2-iodobenzhydrol. Rachel is using Cross-Linked Enzyme Crystals furnished by Altus Biologics to do the resolution via an asymmetric acylation. She has performed the screening and has selected three enzyme systems to optimize. Here are some pictures of her doing the screening. Rachel completed her Ph.D. at Illinois – Champaign-Urbana in the Spring of 2006, and then did a post-doc in Boston.
Rachel continued on with this project through the academic year, along with three other students. Each student attempted to generate chiral nonracemic 2-iodo- benzhydrol, the ultimate precursor to our target.