Multi-step reaction with 13 steps
1: 96 percent / D-(-)-diethyl tartrate ((-)-DET), molecular sieves 4A, titanium(IV) isopropoxide, tert-butyl hydroperoxide (TBHP) / CH2Cl2 / 5 h / -20 °C
2: 1.) potassium hydride / 1.) THF, 23 deg C, 20 min, 2.) 23 deg C, 32 h
3: 93 percent / triethylamine, sulfur trioxide pyridine complex / dimethylsulfoxide / 1 h / 23 °C
4: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 20 min, 2.) 50 deg C, 48 h
5: 100 percent / iron(III) chloride / acetone / 5 h / 23 °C
6: 1.) LDA, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) (MoOPH) / 1.) THF/hexane, -78 deg C, 30 min, 2.) -30 deg C, 10 min
7: 83 percent / tetraethylammonium triacetoxyborohydride, acetic acid / acetonitrile / 1.) -40 deg C, 15 min, 2.) 23 deg C, 1 h
8: 91 percent / 2,6-lutidine / CH2Cl2 / 24 h / 50 °C
9: 1.) triethylamine, BH3*THF, 2.) trimethylamine N-oxide / 1.) THF, 0 deg C, 5 h, 2.) diglyme, 140 deg C, 3 h
10: 90 percent / H2 / 10percent Pd/C / ethanol / 24 h / 23 °C
11: oxalyl chloride, DMSO / CH2Cl2 / 0.33 h / -78 °C
12: acetic acid, water / tetrahydrofuran / 12 h / 60 °C
13: 83 percent / boron trifluoride diethyl etherate / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) 0 deg C, 30 min
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borane-THF; oxalyl dichloride; MoO5*pyridine*HMPA; diethyl (2S,3S)-tartrate; trimethylamine-N-oxide; tetraethylammonium triacetoxyborohydride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; water; hydrogen; sulfur trioxide pyridine complex; iron(III) chloride; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile;
DOI:10.1021/jo00275a020
