Catalytic Enantioselective Silylation of Acyclic and Cyclic Triols: Application to Total Syntheses of Cleroindicins D, F, and C

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...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 3; pp. 547 - 550
Main Authors You, Zhen, Hoveyda, Amir H, Snapper, Marc L
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
Acids, Acyclic - chemistry
Benzofurans - chemical synthesis
Benzofurans - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
enantioselectivity
homogeneous catalysis
Molecular Structure
natural products
Physical Sciences
Science & Technology
silanes
Stereoisomerism
total synthesis
enantioselectivity
ALCOHOLS
natural products
DIHYDROXYLATION
homogeneous catalysis
KINETIC RESOLUTION
silanes
total synthesis
STEREOCONTROLLED SYNTHESIS
DESYMMETRIZATION
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Summary: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.
Bibliography:http://dx.doi.org/10.1002/anie.200805338
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).
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200805338