An efficient route for the synthesis of methyl (−)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate by using baker’s yeast-catalyzed asymmetric reduction

Methyl (−)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate 1, a key synthetic intermediate for the synthesis of terpenoids, was efficiently synthesized by using a baker’s yeast-catalyzed asymmetric reduction of a σ-symmetrical 1,3-cyclohexanedione derivative.

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(−)-Methyl (E)-5-[(2R,3S)-3-hydroxy-2-methyl-1-oxocyclohexyl]-2-pentenoateC13H20O4[α]D20=-19.2 (c 1.06, CHCl3)

(−)-(2S,3S)-1-Acetoxy-1,1-ethylnedioxy-2-methyl-2-(3-acetoxypropyl)cyclohexaneC16H26O6[α]D25=+23.7 (c 1.48, CHCl3)

(+)-Methyl (E)-5-[(2R,3S)-3-(4-bromobenzoyloxy)-2-methyl-1-oxocyclohexyl]-2-pentenoateC20H23BrO5[α]D20=+44.4 (c 1.15, CHCl3)

(+)-Methyl (E)-5-[(2R,3S)-(3-methoxymethoxy-2-methyl-1-oxocyclohexyl)]-2-pentenoateC15H24O5[α]D23=+1.9 (c 1.00, CHCl3)

(+)-Methyl (2R,4aR,5S,8aS)-8a-hydroxy-5-methoxymethyl-4a-methyldeca-hydronaphthalene-1-carboxylateC15H26O5[α]D25=+75.6 (c 0.97, CHCl3)

(−)-Methyl (2R,4aR,5S,8aR)-8a-hydroxy-5-methoxymethyl-4a-methyldecahdronaphthalene-1-carboxylateC15H26O5[α]D23=-31.9 (c 0.35, CHCl3)

(+)-Methyl (4aR,5S)-5-methoxymethyl-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carboxylateC15H24O4[α]D25=+149 (c 0.98, CHCl3)

(−)-Methyl (2R,4aR,5S)-5-methoxymethyl-4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-carboxylateC15H24O4[α]D22=-88.7 (c 0.87, CHCl3)

(+)-Methyl (4aR,5S)-5-hydroxy-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carboxylateC13H20O3[α]D25=+162 (c 0.44, CHCl3)

(+)-Methyl (2S,4aR,5S,8aR)-5-methoxymethyl-1,4a-dimethyldecahydronaphthalene-1-carboxylateC16H28O4[α]D25=+27.6 (c 2.02, CHCl3)

(+)-Methyl (2S,4aR,5S,8aR)-5-hydroxyl-1,4a-dimethyldecahydronaphthalene-1-carboxylateC14H24O3[α]D25=+20.2 (c 2.27, CHCl3)

Methyl (4aR)-4a-methyl-5-oxo-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carboxylateC13H18O3[α]D23=+177 (c 0.98, CHCl3)

(−)-Methyl (2S,4aR,8aR)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylateC14H22O3[α]D25=-35.0 (c 0.82, CHCl3)