Synthesis and in-vivo detection of boronated compounds for use in BNCT

The primary objective of the DOE program at The University of Tennessee Graduate School of Medicine is the development of effective molecular medicine for use in neutron-capture therapy (NCT). The research focuses primarily on the preparation of new boron-rich NCT agents and the technology to detect them in-vivo. The detection technology involves the development of effective magnetic resonance imaging (MRI) and spectroscopy (MRS) techniques for verifying and measuring NCT agents in-vivo. The synthetic program is directed toward the design of novel boron NCT (BNCT) agents which are targeted to the cell nucleus and gadolinium liposomes targeted to the liver. The UT-DOE program is unique in that it has access to both state-of-the-art whole-body and microscopy MRI instruments

Remarkable rate acceleration of SmI(3)-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides

Stereoselective transformation of Baylis-Hillman acetates 1 into corresponding (Z)-allyl iodides 2 has been achieved by treatment of 1 with samarium triiodide in THF. Remarkable rate acceleration of samarium triiodide-mediated iodination of 1 was found when ionic liquid 1-n-butyl-3-methyl-imidazolium tetrafluroborate ([bmim]BF(4)) was used as reaction media in stead of THF. This novel approach proceeds readily at 50 °C within a few minutes to afford (Z)-allyl iodides 2 in excellent yields. A mechanism involving stereoselective iodination of the acetates of Baylis-Hillman adducts by samarium triiodide is described, in which a six-membered ring transition state played a key role in the stereoselective formation of 2