Synthesis of (2,4)-4-Amino-5-hydroxybicyclo[3.1.1]heptane-2-carboxylic Acid via an Asymmetric Intramolecular Mannich Reaction.

Inhibition of human ornithine aminotransferase interferes with glutamine and proline metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.

Design, development, synthesis, and crystal structure of the prototype of a new class of deep blue-fluorescing boron heterocycle estrogen mimics.

To further the development of boron heterocyclic compounds that are useful to medicinal chemistry, we demonstrate how the class of compounds known as the diazaborines can be elaborated to produce an exceptionally close structural mimic of a natural estrogen. After building progressively closer models, a benzyloxy-substituted formylphenylboronic acid was ultimately condensed with a hydroxymethylated β-hydrazinocyclopentenone to give, after debenzylation, an isosteric mimic (diazaborine 1) of the naturally-occurring estrogen equilenin and the prototype of a new class of boron heterocycle estrogen mimics. X-ray crystallography revealed the prototype to be planar, with a transmolecular interoxygen distance virtually identical to that found in equilenin and with a strong hydrogen-bond-donating hydroxyl group.