Molecular Complexity from Aromatics: A Novel, Stereoselective Route to Tricyclo[5.2.2.01,5]undecenones, Tricyclo[6.2.2.01,6]Dodecenones, and [n.3.3]Propellanes
A general stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dieno...
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| Veröffentlicht in: | Journal of organic chemistry 2007-12, Vol.72 (26), p.10155-10165 |
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| container_issue | 26 |
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| container_title | Journal of organic chemistry |
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| creator | Singh, Vishwakarma Sahu, Pramod K Singh, Raj Bahadur Mobin, Shaikh M |
| description | A general stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore. Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage provided an efficient entry into propellanes. |
| doi_str_mv | 10.1021/jo702168s |
| format | Article |
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The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore. 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Org. Chem</addtitle><date>2007-12-21</date><risdate>2007</risdate><volume>72</volume><issue>26</issue><spage>10155</spage><epage>10165</epage><pages>10155-10165</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A general stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore. 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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology General and physical chemistry Organic chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties |
| title | Molecular Complexity from Aromatics: A Novel, Stereoselective Route to Tricyclo[5.2.2.01,5]undecenones, Tricyclo[6.2.2.01,6]Dodecenones, and [n.3.3]Propellanes |
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