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Full Paper
Solid-Phase Synthesis of [5.5]-Spiroketals
Article first published online: 9 JUL 2008
DOI: 10.1002/adsc.200800154
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Sommer, S., Kühn, M. and Waldmann, H. (2008), Solid-Phase Synthesis of [5.5]-Spiroketals. Adv. Synth. Catal., 350: 1736–1750. doi: 10.1002/adsc.200800154
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 9 JUL 2008
- Manuscript Received: 14 MAR 2008
Funded by
- Max-Planck-Gesellschaft
- Fonds der Chemischen Industrie
Keywords:
- asymmetric synthesis;
- chemical biology;
- natural products;
- solid-phase synthesis;
- spiroketals
Abstract
An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramolecular hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochemistry. [5.5]-Spiroketals bearing an additional ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.