In this paper, the synthesis of a novel chiral synthon, 5-(l- menthyloxy)-3-bromo-2 (5H)-furanone (5a) and its application in asymmetric reaction have been investigated. The unusual, functionalized spiro-cyclopropane derivatives containing four stereogenic centers 8a～8d were obrained in good 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 5a, with oxygen nucleophiles under mild conditions. The structure and configuration were established on the basis of their analytical and spectroscopic ([α]^2^0D～, UV, IR, ^1H NMR, ^1^3C NMR, MS) and X-ray crystallographic data.

Key words: FURANONE P, BROMINE COMPOUNDS, MICHAEL ADDITION REACTION, NUCLEOPHILIC REACTION, SUBSTITUTION REACTION, INFRARED SPECTROPHOTOMETRY, ULTRAVIOLET SPECTROPHOTOMETRY, PROTON MAGNETIC RESONANCE SPECTROMETRY, C13 NMR SPECTROMETRY, CONFIGURATION