The invention discloses an asymmetric synthesis method of a dezocine key intermediate, namely, (5R,11S)-5,6,7,8,9,10,11,12-octahydro-3-methoxy-5-methyl-5,11-methylenebenzocyclodecene-13-one. The synthesis method comprises the steps as follows: 7-methoxy-1-methyl-2-tetralone is adopted as a raw material, and an alkylation reaction intermediate, namely, (1R)-1-(5-bormopentyl)-7-methoxy-1-methyl-tetralone, is synthesized in a stereoselective manner under the catalysis of a cinchonidine derivative; ring formation under the alkaline action is performed, and (5R,11S)-5,6,7,8,9,10,11,12-octahydro-3-methoxy-5-methyl-5,11-methylenebenzocycldecene-13-one with high chiral purity is obtained through recrystallization. The method is high in reaction yield, low in cost, mild in condition and suitable for efficient synthesis of dezocine on a large scale.