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Total Synthesis of Spirastrellolide F Methyl Ester—Part 2: Macrocyclization and Completion of the Synthesis

MPS-Authors
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Benson,  S.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Collin,  Marie-Pierre
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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O'Neil,  Gregory W.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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Fenster,  Michaël D. B.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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Goddard,  Richard
Service Department Lehmann (EMR), 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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Citation

Benson, S., Collin, M.-P., O'Neil, G. W., Ceccon, J., Fasching, B., Fenster, M. D. B., et al. (2009). Total Synthesis of Spirastrellolide F Methyl Ester—Part 2: Macrocyclization and Completion of the Synthesis. Angewandte Chemie International Edition, 48(52), 9946-9950. doi:10.1002/anie.200906122.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-8F8F-1
Abstract
Marvel of the sea: A concise and highly convergent total synthesis of the methyl ester of the marine macrolide spirastrellolide F (see picture), which has exquisite antimitotic properties, is reported. In this approach, the northern and the southern hemispheres of this intricate target are stitched together in only two consecutive steps (Suzuki coupling, Yamaguchi lactonization) without any interim protecting-group manipulations.