Multi-step reaction with 34 steps
1.1: 70 percent / N-iodosuccinimide; NaHCO3 / tetrahydrofuran / 36 h / 0 °C
2.1: 99 percent / Et3N; 4-DMAP / CH2Cl2 / 0 - 25 °C
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
4.1: 99 percent / H2 / Raney-Ni / ethanol / 1 h / 25 °C
5.1: 88 percent / H2 / Pd(OH)2/C / ethanol / 3 h / 25 °C
6.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 0 - 25 °C
7.1: Mg / tetrahydrofuran / 2 h / 25 °C
7.2: tetrahydrofuran / 2 h / -78 - 0 °C
8.1: 40.9 g / Dess-Martin periodinane / CH2Cl2 / 4 h / 0 - 25 °C
9.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C
10.1: 96 percent / TBAF / tetrahydrofuran / 48 h / 25 °C
11.1: 97 percent / Et3N; 4-DMAP / CH2Cl2 / 16 h / 0 - 25 °C
12.1: 98 percent / imidazole; 4-DMAP / CH2Cl2 / 0.5 h / 0 °C
13.1: N-methylmorpholine-N-oxide; OsO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 12 h / 25 °C
14.1: 41.5 g / NaIO4 / 2-methyl-propan-2-ol; H2O; various solvents / 5 h / 20 °C / pH 7
15.1: n-BuLi / toluene; tetrahydrofuran / 3 h / -30 °C
15.2: tetrahydrofuran; toluene / 1 h / -30 °C
16.1: 13.2 g / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 0 °C
17.1: 70 percent / TMSOTf / CH2Cl2 / 3 h / -78 - -30 °C
18.1: 95 percent / 4-DMAP; pyridine / CH2Cl2 / 3 h / 0 - 25 °C
19.1: 91 percent / 2,6-lutidine; N-bromosuccinimide; H2O / acetonitrile / 2 h / 25 °C
20.1: 92 percent / NaBH4 / methanol / 0.08 h / -5 °C
21.1: 56 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C
22.1: 97 percent / imidazole / CH2Cl2 / 0.5 h / 0 °C
23.1: 96 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C
24.1: oxalyl dichloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
25.1: n-BuLi / tetrahydrofuran; hexane / 1.33 h / -78 - 0 °C
25.2: 145 mg / tetrahydrofuran; hexane / 2.5 h / 0 °C
26.1: 55 percent / Grubb's catalyst 2nd generation / CH2Cl2 / 12 h / 40 °C
27.1: 86 percent / HF*py; pyridine / tetrahydrofuran / 2 h / 0 °C
28.1: 88 percent / oxalyl dichloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
29.1: LDA / tetrahydrofuran; hexane / 0.17 h / -78 °C
29.2: 71 percent / N-tert-butylbenzenesulfinimidoyl chloride / tetrahydrofuran; hexane / 0.75 h / -78 °C
30.1: 82 percent / NaBH4; CeCl3*7H2O / methanol / 0.5 h / -65 °C
31.1: 4-DMAP; pyridine / CH2Cl2 / 3 h / -10 °C
32.1: 108 mg / Pd2(dba)3*CHCl3; n-Bu3P; LiBH4 / 1,2-dimethoxy-ethane / 1.5 h / 0 °C
33.1: 72 percent / DIBAL-H / CH2Cl2 / 0.33 h / -78 °C
34.1: oxalyl dichloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; N-iodo-succinimide; osmium(VIII) oxide; lithium borohydride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; trifluoroacetic acid; lithium diisopropyl amide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium dihydroxide; nickel;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; various solvents; water; toluene; acetonitrile; tert-butyl alcohol;
24.1: Swern oxidation / 28.1: Swern oxidation / 34.1: Swern oxidation;
DOI:10.1021/ja054750q