Multi-step reaction with 23 steps
1.1: n-BuMgCl / diethyl ether / -60 °C
1.2: toluene / 16 h / Heating
2.1: pyridine / CH2Cl2
3.1: DBU / acetonitrile
3.2: aq. HCl
4.1: NaNO2; Ac2O / acetic acid
5.1: KOH
6.1: p-TsOH / CH2Cl2
7.1: disiamylborane / tetrahydrofuran
7.2: aq. H2O2; NaOH
8.1: imidazole / CH2Cl2
9.1: LiAlH4 / tetrahydrofuran
10.1: TPAP; NMO / acetone
11.1: tetrahydrofuran
12.1: aq. AcOH / tetrahydrofuran
13.1: SO3; pyridine; Et3N / dimethylsulfoxide; CH2Cl2
14.1: CrCl2 / NiCl2 / dimethylformamide / 50 °C
15.1: LiAlH4 / diethyl ether
16.1: pyridine / CH2Cl2
17.1: pyridine / CH2Cl2
18.1: CSA / methanol
19.1: TPAP; NMO / acetone
20.1: tetrahydrofuran
21.1: 99 percent / Grubbs' ruthenium benzylidene catalyst / toluene / 16 h / Heating
22.1: OsO4; DMAP / 2-methyl-propan-2-ol; H2O
23.1: Dess-Martin periodinane / CH2Cl2
With
pyridine; 1H-imidazole; chromium dichloride; dmap; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; sulfur trioxide; butyl magnesium bromide; bis-(1,2-dimethylpropyl)borane; acetic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium nitrite;
Grubbs catalyst first generation; nickel dichloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
1.1: Metallation / 1.2: Cyclization / 2.1: Etherification / 3.1: Elimination / 3.2: Hydrolysis / 4.1: Nitrosation / 5.1: Ring cleavage / 6.1: Addition / 7.1: Hydroboration / 7.2: Oxidation / 8.1: Etherification / 9.1: Reduction / 10.1: Oxidation / 11.1: Wittig olefination / 12.1: Substitution / 13.1: Oxidation / 14.1: Condensation / 15.1: Reduction / 16.1: Etherification / 17.1: Acetylation / 18.1: Substitution / 19.1: Oxidation / 20.1: Wittig olefination / 21.1: Cyclization / 22.1: Addition / 2;
DOI:10.1039/b003757p