The cytology of the parathyroid glands of the rat after bilateral nephrectomy, administration of parathyroid hormone and hypophysectomy An abridgment of a thesis submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the University of Michigan. Supported in part by research grants to Dr. B. L. Baker from the National Institutes of Health, Public Health Service [A-131(C3)] and from the Upjohn Company.

No Abstract.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/49777/1/1091270303_ftp.pd

Synthesis of Novel C/D Ring Modified Bile Acids

Bile acid receptors have been identified as important targets for the development of new therapeutics to treat various metabolic and inflammatory diseases. The synthesis of new bile acid analogues can help elucidate structure–activity relationships and define compounds that activate these receptors selectively. Towards this, access to large quantities of a chenodeoxycholic acid derivative bearing a C-12 methyl and a C-13 to C-14 double bond provided an interesting scaffold to investigate the chemical manipulation of the C/D ring junction in bile acids. The reactivity of this alkene substrate with various zinc carbenoid species showed that those generated using the Furukawa methodology achieved selective α-cyclopropanation, whereas those generated using the Shi methodology reacted in an unexpected manner giving rise to a rearranged skeleton whereby the C ring has undergone contraction to form a novel spiro–furan ring system. Further derivatization of the cyclopropanated steroid included O-7 oxidation and epimerization to afford new bile acid derivatives for biological evaluation