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Total Synthesis of Disciformycin A and B: Unusually Exigent Targets of Biological Significance

MPG-Autoren
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Kwon,  Yonghoon
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schulthoff,  Saskia
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Dao,  Quang Minh
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wirtz,  Conny
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zitation

Kwon, Y., Schulthoff, S., Dao, Q. M., Wirtz, C., & Fürstner, A. (2018). Total Synthesis of Disciformycin A and B: Unusually Exigent Targets of Biological Significance. Chemistry – A European Journal, 24(1), 109-114. doi:10.1002/chem.201705550.


Zitierlink: https://hdl.handle.net/21.11116/0000-0000-31D5-8
Zusammenfassung
The first total synthesis of the potent antibiotic disciformycin B (2) is described, which is exceptionally isomerization-prone and transforms into disciformycin A (1) even under notably mild conditions. To outweigh this bias, the approach to 2 hinged on the use of a silyl residue at C4 to lock the critical double bond in place and hence insure the integrity of the synthetic intermediates en route to 2. This tactic was instrumental for the preparation of the building blocks and formation of the macrocyclic ring via ring closing alkyne metathesis (RCAM). To make the end game successful, however, it proved necessary to cleave the C-silyl protecting group off; it was at this stage that the exceptional sensitivity of the target became fully apparent.