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Toward the Total Synthesis of Spirastrellolide A. Part 1: Strategic Considerations and Preparation of the Southern Domain

MPS-Authors
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Fürstner,  Alois
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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Fasching,  Bernhard
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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Citation

Fürstner, A., Fenster, M. D. B., Fasching, B., Godbout, C., & Radkowski, K. (2006). Toward the Total Synthesis of Spirastrellolide A. Part 1: Strategic Considerations and Preparation of the Southern Domain. Angewandte Chemie International Edition, 45(33), 5506-5510. doi:10.1002/anie.200601654.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0025-AD59-D
Abstract
North and South: The unique biological activity of the natural product spirastrellolide A renders it an attractive lead for anticancer agents. The southern hemisphere (C1–C25) and the northern hemisphere (including the chlorinated [5,6,6]-bis-spiroacetal entity and the lateral C42–C47 chain) are prepared by concise and efficient routes. Consequently, the entire carbon framework of this potent phosphatase inhibitor, which contains 21 chiral centers, is prepared in an optically active form, and an important step toward structure determination by total synthesis is achieved.