Financial support was provided by the NIH (GM-57212) and Z.Y. acknowledges support as a LaMattina Graduate Fellow. We are grateful to Dr. Yu Zhao and Jason Rodrigo (Boston College) for experimental assistance and helpful discussions. Mass spectrometry facilities at Boston College are supported by the NSF (DBI-0619576).
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Catalytic Enantioselective Silylation of Acyclic and Cyclic Triols: Application to Total Syntheses of Cleroindicins D, F, and C†
Article first published online: 15 DEC 2008
DOI: 10.1002/anie.200805338
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
You, Z., Hoveyda, Amir H. and Snapper, Marc L. (2009), Catalytic Enantioselective Silylation of Acyclic and Cyclic Triols: Application to Total Syntheses of Cleroindicins D, F, and C. Angew. Chem. Int. Ed., 48: 547–550. doi: 10.1002/anie.200805338
- †
Publication History
- Issue published online: 29 DEC 2008
- Article first published online: 15 DEC 2008
- Manuscript Received: 31 OCT 2008
Funded by
- NIH. Grant Number: GM-57212
- NSF. Grant Number: DBI-0619576
Keywords:
- enantioselectivity;
- homogeneous catalysis;
- natural products;
- silanes;
- total synthesis
Pick one out of three: Acyclic and cyclic 1,2,3-triols are silylated with exceptional site- and enantioselectivity by a small-molecule catalyst to afford silyl ethers having a neighboring diol moiety. The new process is applied to the enantioselective total syntheses of three cleroindicins, natural products isolated from a plant used in China to battle malaria and rheumatism.