Multi-step reaction with 10 steps
1.1: 87 percent / PPTS; MeOH / [(R,R)Cu(Ph-pybox)](SbF6)2 / CH2Cl2 / 16 h / -78 °C
2.1: 99 percent / K2CO3; MeOH / 17 h / 20 °C
3.1: DIBAL / CH2Cl2 / -50 °C
3.2: pyridine; DMAP / CH2Cl2 / -78 - 0 °C
4.1: 97 percent / BF3*OEt2; TMSOTf; 4 Angstroem mol. sieves / acetonitrile / 1.5 h / -30 - -18 °C
5.1: K2CO3; MeOH / 0.5 h / 20 °C
6.1: pyridine; DMAP / CH2Cl2 / 16 h / 0 - 20 °C
7.1: OsO4; NMO / acetone; H2O
7.2: Pb(OAc)4; Na2CO3 / CH2Cl2 / 0.5 h / 0 - 20 °C
8.1: LiCl; DBU / acetonitrile; CH2Cl2 / 3 h / 20 °C
9.1: Et3N / diethyl ether / 0 - 20 °C
10.1: Jacobsen catalyst; 4 Angstroem mol. sieves / acetone / 3 h
10.2: 38 h
With
pyridine; methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride;
[(R,R)Cu(Ph-pybox)](SbF6)2;
In
diethyl ether; dichloromethane; water; acetone; acetonitrile;
1.1: Evans aldol reaction / 10.1: Jacobsen hetero Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)00754-8