Generous financial support by the MPG, the Chemical Genomics Center (CGC) of the MPG, the Fonds der Chemischen Industrie (Kekulé-stipend to S.B.), the Alexander-von-Humboldt Foundation (fellowship to G.O’N.), and F. Hoffmann–La Roche, Basel, is gratefully acknowledged. We sincerely thank the NMR, X-ray, and chromatography departments of our Institute for excellent support over the entire duration of this project.
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Communication
Total Synthesis of Spirastrellolide F Methyl Ester—Part 1: Strategic Considerations and Revised Approach to the Southern Hemisphere†
Article first published online: 8 DEC 2009
DOI: 10.1002/anie.200906121
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 52, pages 9940–9945, December 21, 2009
Additional Information
How to Cite
O'Neil, G., Ceccon, J., Benson, S., Collin, M.-P., Fasching, B. and 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: 9940–9945. doi: 10.1002/anie.200906121
- †
Publication History
- Issue published online: 15 DEC 2009
- Article first published online: 8 DEC 2009
- Manuscript Received: 30 OCT 2009
Funded by
- MPG
- Chemical Genomics Center (CGC) of the MPG
- Fonds der Chemischen Industrie
Keywords:
- natural products;
- phosphatase inhibitors;
- synthesis design;
- total synthesis
Graphical 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.