Multi-step reaction with 25 steps
1: NaH / dimethylformamide; tetrahydrofuran
2: HCl / methanol; diethyl ether / 0 °C
3: (COCl)2, DMSO, i-Pr2NEt / -78 - -30 °C
4: 73 percent / TiCl2(O-i-Pr)2 / CH2Cl2 / -78 - 0 °C
5: Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 °C
6: HCl
7: DIBAL-H / CH2Cl2 / -78 °C
8: 1.) Bu2BOTf, i-Pr2NEt / 1.) CH2Cl2, 0 deg C, 2.) CH2Cl2, -78 deg C
9: 100 percent / (COCl)2, DMSO, i-Pr2NEt / -78 - 0 °C
10: 82 percent / TsOH / acetonitrile / -22 °C
11: 100 percent / (COCl)2, DMSO, Et3N / -78 - 0 °C
12: LDA / 1 h / -78 °C
13: LiOOH / tetrahydrofuran; dimethylformamide; H2O / 0 - 23 °C
14: aq. OsO4, NMO / tetrahydrofuran; 2-methyl-propan-2-ol
15: aq. NaIO4, NaHCO3 / tetrahydrofuran; 2-methyl-propan-2-ol
16: 1.) Et3N, 2.) Et3NHOAc
17: 1.) c-hex2BCl, Me2NEt / 1.) Et2O, 0 deg C, 2.) Et2O, from -78 deg C to 0 deg C
18: imidazole / CH2Cl2
19: Et3NHOAc
20: (2,4,6-Cl3PhCO)2O, i-Pr2NEt, DMAP / benzene
21: 68 percent / 3-ClPhNCO, i-Pr2NEt / benzene / 90 °C
22: NaHMDS / tetrahydrofuran
23: aq. AgNO3, 2,6-lutidine / tetrahydrofuran
24: HF*pyr / tetrahydrofuran
25: 99 percent / aq. TsOH / acetonitrile
With
1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; titanium(IV) dichlorodiisopropylate; oxalyl dichloride; lithium hydroperoxide; N,N-dimethyl-ethanamine; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; dicyclohexylboron chloride; sodium hexamethyldisilazane; triethylammonium acetate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; m-chlorophenyl isocyanate; lithium diisopropyl amide; 2,4,6-trichlorobenzoic anhydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja990789h