Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest

Anderl, Felix; Größl, Sylvester; Wirtz, Conny; Fürstner, Alois

doi:10.1002/anie.201805125

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Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest

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

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Größl, Sylvester
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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引用

Anderl, F., Größl, S., Wirtz, C., & Fürstner, A. (2018). Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest. Angewandte Chemie International Edition, 57(33), 10712-10717. doi:10.1002/anie.201805125.

引用: https://hdl.handle.net/21.11116/0000-0001-E5EE-1

要旨

The assigned structure of the dinoflagellate-derived toxin belizentrin was prepared by total synthesis in form of the corresponding methyl ester for stability reasons. The successful route features an unusual solution for the preparation of a recalcitrant ylid on a C-glycosidic segment; moreover, it involves an asymmetric hetero-Diels/Alder reaction en route to the tertiary hemiacetal substructure, a Negishi cross coupling of two elaborate building blocks, and a macrocyclization based on an intramolecular aminolysis of a spirolactone. A modified Kocienski olefination ultimately allowed the polyol side chain to be attached to the macrocycle, although this transformation faced the exceptional base-sensitivity of this polyunsaturated target compound.