Multi-step reaction with 21 steps
1.1: 36.0 g / (DHQ)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C
2.1: PPTS / CH2Cl2 / 1.5 h / 20 °C
3.1: 21.77 g / TBAF / tetrahydrofuran / 2 h / cooling
4.1: 59 percent / Ph3P; DIAD / tetrahydrofuran / 24 h / 20 °C
5.1: 60 percent / MCPBA / CH2Cl2 / 16 h / 20 °C
6.1: 84 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / 2.5 h / -78 - 20 °C
7.1: 90 percent / DIBAL-H / CH2Cl2 / 1.5 h / -78 °C
8.1: 96 percent / Dess-Martin periodinane; pyridine / CH2Cl2; H2O / 3 h / 20 °C
9.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
9.2: 99 percent / tetrahydrofuran / 1 h / -78 °C
10.1: Hg(OAc)2 / tetrahydrofuran; H2O / 1 h / cooling
10.2: 72 percent / NaBH4 / tetrahydrofuran; H2O / 2 h
11.1: 99 percent / imidazole; DMAP / dimethylformamide / 0.5 h
12.1: 37 percent / PPTS / methanol / 3 h / Heating
13.1: Et3N; MsCl / CH2Cl2 / 0.83 h / 0 °C
13.2: 81 percent / DBU / CH2Cl2 / 4 h / 20 °C
14.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / potassium osmate dihydrate; K2S2O8 / 2-methyl-propan-2-ol; H2O / 16 h / cooling
15.1: 91 percent / PPTS / methanol; CH2Cl2 / 2.08 h / -78 - 20 °C
16.1: 59 percent / KHMDS / tetrahydrofuran; toluene / 16 h / cooling
17.1: 83 percent / KH / tetrahydrofuran; various solvent(s) / 2 h
18.1: 99 percent / TBAF / tetrahydrofuran / 16 h / 20 °C
19.1: 67 percent / Ph3P; iodine; imidazole / benzene / 1 h / 20 °C
20.1: 70 percent / i-Pr2NEt / acetonitrile / 48 h / 90 °C
21.1: KHMDS / toluene / 0.5 h / -78 °C
21.2: 26 percent / toluene / -78 - 20 °C
With
pyridine; 1H-imidazole; dmap; Hydroquinone 1,4-phthalazinediyl diether; di-isopropyl azodicarboxylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; methanesulfonyl chloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III);
potassium osmate(VI); dipotassium peroxodisulfate; potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;
4.1: Mitsunobu reaction / 6.1: Julia-Kocienski coupling / 8.1: Dess-Martin oxidation / 9.2: Wittig olefination / 21.2: Wittig olefination;
DOI:10.1021/jo062513f