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DOI: 10.1055/s-2003-41415
Introduction of Bicyclic Ketal Chemistry: Synthesis and Transformation Reaction of 6,8-Dioxabicyclo[3.2.1]octane Skeletal System
Publication History
Publication Date:
28 August 2003 (online)
Abstract
A stereo- and regioselective bicyclic ketal synthesis and several facile one-pot transformations of bicyclic ketals are described with plausible mechanisms. Products have included δ,ε-unsaturated ketones, mono- and diacetoxy ketones, transketalized ketones, cis- and trans-cyclic ethers, 1,5-diketones, cis-1,2-cyclopentanediols, 2,6-disubstituted pyridines, 2,3,6-trisubstituted pyridines, and conjugated and nonconjugated cyclohexenones.
1 Introduction
2 Synthesis of Bicyclic Ketal Structure
2.1 Stereoselective Introduction of C-7 Alkyl Group
2.2 Application to Natural Products Synthesis
2.3 Functionalization of Bicyclic Ketal Structure
2.3.1 C1 Alkylation
2.3.2 C4 Alkylation
2.3.3 C5 Alkylation
2.3.4 [3,3]-Sigmatropic Rearrangement of Dihydropyran Derivatives
3 Transformation Reactions of Bicyclic Ketal Structure
3.1 Selective C-O Bond Cleavage
3.1.1 Synthesis of Enone, Monoacetate, and Diacetate Derivatives
3.1.2 Synthesis of Cyclic Ethers
3.2 Rearrangement Reaction to 1,5-Diketones
3.2.1 Synthesis of 1,5-Diketones
3.2.2 Direct Synthesis of cis-1,2-Cyclopentanediols
3.2.3 Direct Synthesis of 2,6-Disubstituted Pyridines
3.2.4 Selective Enolization
3.3 Synthesis and Rearrangement Reactions of Ketal-Lactone Structure
4 Conclusion
Key words
bicyclic ketal - 6,8-dioxabicyclo[3.2.1]octane - Lewis acid - one-pot transformation - C-O bond cleavage
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References
Undesirable side products and non-homogeneous systems could be avoided by dilution with THF to 0.1-1.0 M, the anions were stable in THF once formed.