Monatshefte f€ ur Chemie 135, 729–733 (2004) DOI 10.1007/s00706-003-0120-3 Synthesis of Some Novel c-Spirolactones Javad Azizian  , Ali R. Karimi, Hamedeh Arefrad, Ali A. Mohammadi, and Mohammad R. Mohammadizadeh Department of Chemistry, Faculty of Science, Shahid Beheshti University, P.O. Box 19395-4716, Tehran, Iran Received June 20, 2003; accepted (revised) July 11, 2003 Published online April 22, 2004 # Springer-Verlag 2004 Summary. We report on the addition of dialkyl acetylenedicarboxylate to 1-alkylisatins or tryptan- thrine in the presence of triphenylphosphine which leads to highly functionalised novel unsaturated -spirolactones. Keywords. -Spirolactones; Triphenylphosphine; 1-Alkylisatin; Tryptanthrine. Introduction -Spirolactones are an important class of molecules owing to their interesting structures and biological activities [1]. The lactone moiety is also present in many natural products [2], especially in insect pheromones [3], antifungal sub- stances, and flavor components that occur in essential oils [4]. Recently, -spirol- actones have been the subject of interest because of their effect as aldostrone inhibitors [5]. Systematic investigations of spiroindoles and indoloquinazolines are of interest due to their broad spectrum of biological activities [6]. Because of the pharmaco- logical interest in these compounds, which belong to the indole and indoloquinazo- line family [7] we have synthesized some novel -spirolactone derivatives from 1-alkylisatins and tryptanthrine. These molecules might show enhanced biological activities because they incorporate both indole and indoloquinazoline or lactone moieties. The stochiometric as well as the catalytic use of phosphines and a variety of other organophosphorus compounds has become an integral part of organic synthe- sis [8]. In particular, triphenylphosphine (TPP) acts as a catalyst in various iso- merization reactions of alkynes and allenes [9], and in the nucleophilic addition of malonate to methyl propiolate [10]. The addition of TPP to electron deficient  Corresponding author. E-mail: J-Azizian@cc.sbu.ac.ir