Nonenzymic polycyclization of analogues of oxidosqualene with a preformed C-ring |
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Authors: | Winne Johan M De Clercq Pierre J Milanesio Marco Pattison Philip Viterbo Davide |
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Institution: | Ghent University, Department of Organic Chemistry, Krijgslaan 281 (S4), B-9000 Gent, Belgium. |
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Abstract: | Some nonenzymic epoxide-initiated polyolefin cyclization are reported. The presented molecules are partially constrained analogues of (3S)-oxidosqualene, the natural substrate to many important cyclase enzymes. These model compounds feature a preformed C-ring with built-in stereochemical information. The experimental results allow for an instructive comparison with the enzymic processes, particularly those of the cyclases in steroid biosynthesis (i.e. lanosterol synthase). |
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