Abstract
A new concept of cyclic conjugation as a modification of the Huckel rule has proven to be useful as a general method for predicting thermal stabilities and electronic properties of unsaturated cyclic organic molecules. We have been applying this concept to the design of reagents such as p-benzoquinone, polyquinones, and 1, 4-dithiins. Our efforts for the molecular design have relied extensively on the use of pericyclic reactions as pivotal steps in the total synthesis of polycyclic natural products incorporating fused heterocyclic subunits, targets that traditionally have provided fertile grounds for the development of new synthetic strategies. In order to obtain a quantitative understanding of the linkage between drug-bioreceptor complex formation, we have investigated the design and synthesis for the biologically active compounds (receptor probes) as follows : 1) the design and structure-activity relationship of a series of S-activated opioid agonist and antagonist ligands, 2) the design and synthesis of crowned morphine as the opioid receptor probes and 1, 4-benzoquinones as ionophore-dienophile combined systems, 3) synthesis of the base stacking and hydrogen-bonded nucleic acid base pair.
