Multi-step reaction with 10 steps
1: 53 percent / O3, sodium borohydride / ethanol / -78 - 0 °C
2: 82 percent / lipase AK / benzene / Ambient temperature
3: 90 percent / Et3N, 4-DMAP / CH2Cl2 / Ambient temperature
4: 1.) NaBH4; 2.) lithium aluminum hydride / 1.) DMSO, 60 deg C; 2.) THF, 0 deg C
5: 87 percent / i-Pr2NEt, 4-DMAP / Ambient temperature
6: 94 percent / 18-crown-6 / dimethylsulfoxide / 60 °C
7: 1.) diisobutylaluminum hydride; 2.) 10percent HCl / CH2Cl2; hexane
8: NaBH4 / methanol / 0 °C
9: 1.) o-nitrophenylselenylcyanide, tri-n-butylphosphine; 2.) hydrogen peroxide / 1.) THF, r.t.; 2.) THF, r.t.
10: 100 percent / AD-mix-α, aq. t-BuOH / 0 °C
With
hydrogenchloride; dmap; sodium tetrahydroborate; AD-mix-α; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; lipase AK; 18-crown-6 ether; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol;
In
methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.3987/com-97-s39