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Communication | Regular issue | Vol 16, No. 9, 1981, pp.1463-1468
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1463
2-Azabicyclo[3.2.0]heptane-3,4-diones (6). A Novel Method of Regio-controlled Synthesis of Functionalized Hydroindoles and Erythrinan Derivatives

Takehiro Sano,* Jun Toda, Yoshie Horiguchi, Kazue Imafuku, and Yoshisuke Tsuda

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


A regio-controlled synthesis of functionalized hydroindoles from a Δ2-pyrrolinedione and its application to the synthesis of erythrinan skeleton were described. The method is to construct with [2+2] photocycloaddition of a trimethylsilyloxybutadiene to a Δ2-pyrrolinedione followed by thermal [1,3]-rearrangement to yield a hydroindole silyl enol ether, which is isomeric with the hydroindole silyl enol ether obtained by Diels-Alder cyclization between the same substrates.