Cholic Acid as an Architectural Component in Biomimetic/Molecular Recogition Chemistry; Synthesis of "Cholaphanes" With Facial Differentiation of Functionality

Article abstract of DOI:10.1016/S0040-4020(01)80187-3

Facially-differentiated cholaphanes (2) were synthesized in good yields from cholic acid (1).Key steps were the selective 3,7-bis-O-acetylation of methyl cholate (3), the 12-O-benzylation of diacetate 4, and the introduction of a 3β-(p-aminomethyl)phenyl substituent using an arylmanganese reagent and employing the novel ''benzostabase'' N-protection methodology.