1-Aminoadamantane is known to be a potent antiviral agent. Its symmetric shape, lipophilic solubility, and nucleophilic head group are recognized as responsible for its efficacious behavior toward influenza viruses. The goals of this proposal are to develop expedient routes to unusual and complex spherical hydrocarbons with a view to their proper functionalization as amino derivatives. Top priority is to be given to a more expedient and/or efficient synthesis of the pentagonal dodecahedrane in order to acquire its -NH-2, -CH2NH2, and -CH-2CH-2NH-2 derivatives for biological evaluation. A variety of procedures are described that are expected to afford these target compounds. The development of derivatization chemistry will not stop here, but activity will be suitably expanded to include bromination and seleneylation (precursors to dodecahedrane), carbocation generation (means for acquiring otherwise inaccessible disubstituted derivatives), and ring expansion to homododecahedranes and the azahomododecahedrane ring system. Attention will also be given to the synthesis of tethered dodecahedranes, the ditrigonal structural isomer, and the larger spherical homologs pentakai- and hexakaidecahedrane. Entry to spherical molecules of intermediate size will also occupy our attention. These include p-[4-2,5-8]decahedrane, p-[3-2,5-6]octahedrane and select amino derivatives. The new synthetic methodology to be developed promises to be of substantive value in delineating the degree of ease and rapidity with which spherical molecules of the above type will become available.
| Lagerwall, D R; Gallucci, J C; Paquette, L A (1991) Structure of diethyl 1,2,3,3b,4a,5,6,7,8,8a,8b,9-dodecahydro-1,5-dioxo-4,8,9-metheno-4H-cycl openta [1,2-a:4,3-a']dipentalene-4,10-dicarboxylate. Acta Crystallogr C 47 ( Pt 9):1868-72 |
| Gallucci, J C; Taylor, R T; Kobayashi, T et al. (1989) X-ray crystallographic analysis of the structural distortions induced by substitution and annulation of the dodecahedrane nucleus. Acta Crystallogr C 45 ( Pt 6):893-8 |
