Total Synthesis of Amphidinolide F

Valot, Gaëlle; Regens, Christopher S.; O'Malley, Daniel P.; Godineau, Edouard; Takikawa, Hiroshi; Fürstner, Alois

doi:10.1002/anie.201301700

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Total Synthesis of Amphidinolide F

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

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Regens, Christopher S.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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O'Malley, Daniel P.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Takikawa, Hiroshi
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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anie_201301700_sm_miscellaneous_information.pdf
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引用

Valot, G., Regens, C. S., O'Malley, D. P., Godineau, E., Takikawa, H., & Fürstner, A. (2013). Total Synthesis of Amphidinolide F. Angewandte Chemie International Edition, 52(36), 9534-9538. doi:10.1002/anie.201301700.

引用: https://hdl.handle.net/11858/00-001M-0000-0014-A3B5-8

要旨

Orchestrated yet nonconsonant: The challenge posed by the “umpoled” 1,4-dioxygenation pattern characteristic for the polyketide frame of amphidinolide F was mastered by a late-stage ring-closing alkyne metathesis followed by a directed transannular hydration under the aegis of a carbophilic π-acid catalyst. This concordant strategy enabled a concise total synthesis of this enticing marine natural product.