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Journal Article

Metathesis at an Implausible Site: A Formal Total Synthesis of Rhizoxin D

MPS-Authors
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Karier,  Pol
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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

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Wille,  Christian
Research Department Fürstner, 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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Supplementary Material (public)

anie201812096-sup-0001-misc_information-1.pdf
(Supplementary material), 6MB

Citation

Karier, P., Ungeheuer, F., Ahlers, A., Anderl, F., Wille, C., & Fürstner, A. (2019). Metathesis at an Implausible Site: A Formal Total Synthesis of Rhizoxin D. Angewandte Chemie International Edition, 58(1), 248-253. doi:10.1002/anie.201812096.


Cite as: https://hdl.handle.net/21.11116/0000-0002-E57A-3
Abstract
The new approach to the anticancer agent rhizoxin D described herein does not cohere with the conventional logic of metathesis, according to which macrocycles are best closed at a disubstituted olefinic site; rather, the trisubstituted C11−C12 alkene flanked by an allylic ‐OH group served as the pivot point for synthesis. This motif was attained in good yield and excellent selectivity by a sequence of alkyne metathesis, trans‐hydrostannation and cross coupling. Because the exact same substructure is prominently featured in numerous other natural products, the underpinning strategy, though unusual, might bear more general relevance.