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Journal Article

Total Synthesis of Amphidinolide F

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons132854

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58920

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132856

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132858

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132860

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

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

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Supplementary Material (public)

anie_201301700_sm_miscellaneous_information.pdf
(Supplementary material), 7MB

Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A3B5-8
Abstract
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.