Singh Vishwakarma, Sahu Pramod K, Singh Raj Bahadur, Mobin Shaikh M
Department of Chemistry and National Single Crystal X-ray Diffraction Facility, Indian Institute of Technology, Bombay, Mumbai 400076, India.
J Org Chem. 2007 Dec 21;72(26):10155-65. doi: 10.1021/jo702168s. Epub 2007 Nov 30.
A general stereoselective route to functionalized and substituted tricyclo [5.2.2.0(1,5)]undecenones, tricyclo[6.2.2.0(1,6)]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[5.2.2.0(1,5)]undecenones and tricyclo[6.2.2.0(1,6)]dodecenones endowed with a beta,gamma-enone chromophore. Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage provided an efficient entry into propellanes.
报道了一种从简单的芳香族前体出发，立体选择性地合成官能化和取代的三环[5.2.2.0(1,5)]十一碳烯酮、三环[6.2.2.0(1,6)]十二碳烯酮以及[3.3.3]-和[4.3.3]螺旋烷的通用方法。该方法包括稠合的环己-2,4-二烯酮与各种丙烯酸酯的生成和环加成，随后对所得三环加合物进行处理，从而得到具有β,γ-烯酮发色团的官能化三环[5.2.2.0(1,5)]十一碳烯酮和三环[6.2.2.0(1,6)]十二碳烯酮。三环发色体系的光化学反应随后进行还原裂解，为螺旋烷的合成提供了一条有效途径。
