The present studies describe, as a primary goal, our recent progess toward the
synthesis of morphine alkaloids from aromatic precursors. Model substrates were
synthesized which allowed investigation into Diels-Alder, radical cascade, and
palladium-catalyzed bond-forming reactions as possible routes to the morphine alkaloid
skeleton. As a secondary objective, three separate series of aromatic substrates were
subjected to whole-cell oxidation with Escherichia coli JM 109 (pDTG601), a
recombinant organism over-expressing the enzyme toluene dioxygenase. Included in
this study were bromothioanisoles, dibromobenzenes, and cyclopropylbenzene
derivatives. The products of oxidation were characterized by chemical conversion to
known intermediates. The synthetic utility of one of these bacterial metabolites, derived
from oxidation of o-dibromobenezene, was demonstrated by chemical conversion to (-)conduritol
E
