Multi-step reaction with 27 steps
1.1: 98 percent / LiI; LiAlH4 / diethyl ether / -100 - 0 °C
2.1: 97 percent / AcOH / H2O / 5 h / 40 °C
3.1: 70 percent / NaHCO3; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C
4.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 25 °C
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
6.1: 99 percent / H2; Raney-Ni catalyst / ethanol / 1 h / 25 °C
7.1: 88 percent / H2 / Pd(OH)2/C / ethanol / 3 h / 25 °C
8.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 0 - 25 °C
9.1: Mg / tetrahydrofuran / 2 h / 25 °C
9.2: tetrahydrofuran / 2 h / -78 - 0 °C
10.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 4 h / 0 - 25 °C
11.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C
12.1: N-methylmorpholine-N-oxide; OsO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 14 h / 25 °C
12.2: 100 percent / NaIO4; aq. saline solution buffer / tetrahydrofuran; 2-methyl-propan-2-ol / 5 h / 25 °C
13.1: n-BuLi / tetrahydrofuran; toluene / 3 h / -30 °C
13.2: tetrahydrofuran / 1 h / -30 °C
14.1: 13.2 g / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 0 °C
15.1: 85 percent / TMSOTf / CH2Cl2 / 3 h / -78 - -30 °C
16.1: 95 percent / pyridine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
17.1: 91 percent / 2,6-lutidine; N-bromosuccinimide / acetonitrile; H2O / 2 h / 25 °C
18.1: 92 percent / NaBH4 / methanol / 0.08 h / -5 °C
19.1: 56 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C
20.1: 80 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -78 - 0 °C
21.1: 83 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C
22.1: 90 percent / Pd(PPh3)4; n-Bu3SnH / tetrahydrofuran / 0.75 h / 25 °C
23.1: 92 percent / diisobutylaluminum hydride / CH2Cl2 / 0.33 h / -78 °C
24.1: 92 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -78 - 0 °C
25.1: diethyl ether; tetrahydrofuran / 1 h / 25 °C
26.1: pyridine; 4-DMAP / CH2Cl2 / 3 h / 0 °C
27.1: 82 percent / lithium diisopropylamide; hexamethylphosphoramide; t-BuMe2SiCl / tetrahydrofuran / 72 h / -78 - 25 °C
With
pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; Raney-Ni catalyst; hydrogen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; tert-butyldimethylsilyl chloride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; trifluoroacetic acid; lithium iodide; lithium diisopropyl amide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;
20.1: Swern oxidation / 24.1: Swern oxidation / 27.1: Ireland-Claisen rearrangement;
DOI:10.1021/ja0547477