Multi-step reaction with 16 steps
1: 90 percent / DMAP, Et3N / CH2Cl2 / 1.5 h / 0 °C
2: 1.) Py*HCl, (Cl2CHCO)2O, 2.) Na2CO3 / 1.) xylene, 150-155 deg C, 0.5 h, 2.) acetone, H2O, 25 deg C, 14 h
3: pyridine / 5 h / 0 °C
4: 1.) PhSeSePh, NaBH4, 2.) mCPBA, Na2CO3 / 1.) EtOH, reflux, 1.5 h, 2.) THF, 25 deg C, 24 h
5: MeSOPh / CH2Cl2 / -78 °C
6: 94 percent / thiourea, NaHCO3 / ethanol / 18 h / 70 °C
7: 85 percent / ClCH2CO2H, DEAD, PPh3 / 18 h / 25 °C
8: 99 percent / AgNO3 / dimethylformamide / 0.08 h / 25 °C
9: 1.) OsO4, (S,S)-N,N-di<(mesitylene)methyl>-1,2-diphenyl-1,2-ethylenediamine, 2.) aq. NaHSO3 / 1.) CH2Cl2, -100 deg C, 0.5 h, 2.) THF, reflux
10: 91 percent / NBS / tetrahydrofuran / 0.5 h / -78 °C
11: n-Bu3SnH / 80 °C
12: imidazole / dimethylformamide / 1 h / 25 °C
13: aq. KHCO3 / methanol / 3 h / Heating
14: Brown-Jones oxidation
15: 76 percent / PTAB / tetrahydrofuran / 0.25 h / 0 °C
16: 93 percent
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; racemic methyl phenyl sulfoxide; PTAB; diphenyl diselenide; tri-n-butyl-tin hydride; pyridine hydrochloride; sodium hydrogencarbonate; sodium carbonate; potassium hydrogencarbonate; silver nitrate; sodium hydrogensulfite; dichloroacetic anhydride; (1S,2S)-1,2-diphenyl-N1,N2-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; thiourea; chloroacetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00081a050