In this paper, the unusual spiro-cyclopropane bis-lactones containing four stereogenic centers 4a-4d were obtained in 25%-48% yields with d.e.≥98% via tandem double Michael addition/internal nucleophilic substitution of the novel chiral synthon, 5-l-menthyloxy- 3-bromo-2-(5H)-furanone 1, with nitrogen nucleophiles under mild conditions. The structure and configuration were established on the basis of their analytical and spectroscopic ([α]~D^2^0, UV, IR, ^1H NMR, ^1^3C NMR, MS and X-ray crystallographic) data. These results provide a valuable synthetic route to some complex molecules containing spiro-cyclopropane skeleton with multiple chiral centers.

Key words: CYCLOPROPANE P, SPIRO COMPOUNDS, LACTONES, NUCLEOPHILIC REACTION, SUBSTITUTION REACTION, OPTICAL PROPERTIES