The S (+) sulcatol(1) was prepared in 4 steps. Sodium phenyl sulfinate was reacted with bromoacetone in ethanol to give 1 phenylsulfonyl 2 propanone(2). Alkylation of (2) by 1 chloro 3 methyl 2 butene(3) in the presen...The S (+) sulcatol(1) was prepared in 4 steps. Sodium phenyl sulfinate was reacted with bromoacetone in ethanol to give 1 phenylsulfonyl 2 propanone(2). Alkylation of (2) by 1 chloro 3 methyl 2 butene(3) in the presence of K 2CO 3 through solid liquid PTC in DMF at 40～50 ℃ gave 3 phenylsulfonyl 6 methyl 5 heptene 2 one(4). The sulfone moiety of (4) was removed by Raney Ni reduction under mild conditions and the key intermediate prochiral 6 methyl 5 heptene 2 one(5) was obtained. Sulcatol(1) with optical purity of 94%e.e. was obtained by Baker′s yeast mediated reduction of (5).展开更多
文摘The S (+) sulcatol(1) was prepared in 4 steps. Sodium phenyl sulfinate was reacted with bromoacetone in ethanol to give 1 phenylsulfonyl 2 propanone(2). Alkylation of (2) by 1 chloro 3 methyl 2 butene(3) in the presence of K 2CO 3 through solid liquid PTC in DMF at 40～50 ℃ gave 3 phenylsulfonyl 6 methyl 5 heptene 2 one(4). The sulfone moiety of (4) was removed by Raney Ni reduction under mild conditions and the key intermediate prochiral 6 methyl 5 heptene 2 one(5) was obtained. Sulcatol(1) with optical purity of 94%e.e. was obtained by Baker′s yeast mediated reduction of (5).
