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Communication | Regular issue | Vol 22, No. 1, 1984, pp.49-52
Published online, 1st January, 1970
DOI: 10.3987/R-1984-01-0049
A Novel Erythrinan and Homoerythrinan Synthesis by Tetra-n-butylammonium Fluoride Induced Oxy-vinyl 1,3-Shift. Synthesis of a 6-Methoxycarbonyl-2,8-dioxo-1,7-cyclo-B-homoerythrinan, a Potential Intermediate to Schelnammera Alkaloids

Takehiro Sano,* Jun Toda, Yoshisuke Tsuda, and Takeshi Ohshima

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

Abstract

Photocycloaddition of trimethylsilyloxybutadiknes to an isoquinolinopyrrolinedione followed by treatment of the [2+2]adduct with TBAF furnished erythrinan derivatives in high yields as a result of 1,3-shift. By this method, a practical synthetic route to B-homoerythrinan derivatives is now opened and a 6-methoxycarbonyl-2,8-dioxo-l,7-cyclo-B-homoerythrinan 20, a potential intermediate to Schelhammera alkaloids, was synthesized in an acceptable yield.