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So far, spontaneous resolution has been rarely reported.However, an amazing instance of this phenomenon has been discovered in our laboratory.Enantiomers (S,R) of cyclic γ-alkenyl alcohol (1) could be obtained (optical purity ＞ 99％ ee) from the racemic mixture and crystals of both enantiomers could be recognized and separated according to their physical appearance by the naked eye.On the basis of this work, we subsequently explored the asymmetric synthesis of octahydrobenzofuran core structure with three contiguous stereogenic centers and have also established their absolute configurations by single crystal X-ray analysis of 3.