Abstract:
The present studies describe our recent work on expanding the use of the Burgess
reagent and its reaction with oxiranes. Several new variants of the Burgess reagent and its
chiral auxiliary version were evaluated for their thermal stability by NMR spectroscopy.
Three new versions of the reagent were synthesized and their stability was determined.
The reactivity of all five Burgess reagents was compared in a dehydration reaction and
reactions with epoxides and diols.
Progress toward a chemoenzymatic synthesis of morphine is also included in this
report. The synthesis began with the whole cell oxidation of bromobenzene by
Escherichia coli JMI09(pDTG601). The preparation of several precursors for a key step
involving the lohnson-Claisen rearrangement and progress toward the total synthesis are
described.
