In the 15th Symposium of The Chemistry of Natural products which was held in 1971 at Nagoya, we reported the chemical conversion of enmein (1) into diol (2) and also a partial synthesis of enmein from (2). Now, we succeeded in the synthesis of racemate (36) and the chemical conversion of its optically active enantiomer (41) into (2). Thus, a total synthesis of enmein was accomplished. 5-Methoxy-2-tetralone was converted into (5), from which the desirable compounds (10) and (11) were derived through several steps of reactions shown in Chart 2. The structures of these compounds were chemically confirmed as shown in Chart 3. The Birch reduction with (10) proceeded exceedingly efficiently, and the desired ketone (23) was obtained in good yield. Some considerations about the intramolecular participations of hydroxy groups were tried. The stereoselective construction of ring D was achieved by the route shown in Chart 6. The product (36) was identified with its optically active enantiomer (41) which was derived via (39) and (40) from enmein. Compound (41) was converted into (2) by tetrahydropyranylation and dehydration followed by ethylene-acetalization as shown in Chart 7.