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Total Synthesis of Spirastrellolide F Methyl Ester—Part 1: Strategic Considerations and Revised Approach to the Southern Hemisphere

MPS-Authors
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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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Benson,  Stefan
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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Fasching,  Bernhard
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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[271]SI.pdf
(Supplementary material), 384KB

Citation

O'Neil, G. W., Ceccon, J., Benson, S., Collin, M.-P., Fasching, B., & Fürstner, A. (2009). Total Synthesis of Spirastrellolide F Methyl Ester—Part 1: Strategic Considerations and Revised Approach to the Southern Hemisphere. Angewandte Chemie International Edition, 48(52), 9940-9945. doi:10.1002/anie.200906121.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-8F8D-5
Abstract
In readiness for closure: To ensure optimal convergence in the projected total synthesis of spirastrellolide F, the building block representing the southern hemisphere was prepared with a free carboxylic acid and an enol triflate (Tf) terminus (see picture). This unusual pattern allows the 38-membered macrocyclic core of this potent antimitotic agent to be constructed, while keeping late-stage protecting-group manipulations to a minimum.