Trimolecular adducts resulting from condensation between indolin‐2‐one (or indoline‐2‐thione), (aryl)aldehydes, and Meldrum’s acid are useful intermediates for the synthesis of either 1,2,3,4‐tetrahydro‐1‐thiacarbazoles or spiro[pyrrolidino‐3,3′‐oxindoles] related to the natural product horsfiline. These latter compounds were obtained in a three‐step procedure characterized by acyl azide formation, Curtius rearrangement, and subsequent thermal spiro cyclization. The relative stereochemistry of the spiro derivatives was determined by comparison of NOESY data and calculated conformational analyses. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)