CHOLAPHANES ET-AL - STEROIDS AS STRUCTURAL COMPONENTS IN MOLECULAR ENGINEERING

As a rigid, chiral, and extended structural fragment, the steroid nucleus is an excellent starting point for the design of preorganized molecular frameworks. Units derived from cholesterol and cholic acid have been used to provide appendages and spacers, and to organize functional group arrays for studies in biomimetic chemistry. Recent work has shown that cholic acid may also be elaborated into macrocycles such as the 'cholaphanes' of the title. The inward-directed functional groups in these molecules result in distinctive properties, including the molecular recognition of carbohydrate derivatives in organic media.