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Synthesis of the C21-C34 fragment of antascomicin B |
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| Authors: | Hutchison John M Gibson Andrew S Williams David T McIntosh Matthias C |
| Institution: | University of Arkansas, 119 Chemistry Building, Fayetteville, AR 72701, USA |
| Abstract: | The C21-C34 fragment of the potent FKBP12-binding macrolide antascomicin B was prepared using Ireland-Claisen and allylic diazene rearrangements to establish the C26/C27 and the C23 stereocenters, respectively. Directed hydrogenation installed the C29 β-configuration. The fragment possesses 7 of the 11 fixed stereocenters contained in the natural product. |
| Keywords: | Ireland-Claisen rearrangement Allylic diazene rearrangement Directed hydrogenation Natural product |
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