Multi-step reaction with 18 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran; CH2Cl2 / 0.25 h / 20 °C
1.2: tetrahydrofuran; CH2Cl2 / 18 h / 65 °C
2.1: LiHMDS / diethyl ether / 0.25 h / 0 °C
2.2: diethyl ether / 24 h / 0 - 20 °C
3.1: Fe(acac)3 / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / -20 °C
4.1: DIBAL-H / CH2Cl2 / 0.33 h / -78 °C
5.1: MnO2 / diethyl ether / 19 h / 20 °C
6.1: Sn(OTf)2; N-ethylpiperidine / CH2Cl2 / 4 h / -55 °C
6.2: CH2Cl2 / 0.5 h / -78 °C
7.1: 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
8.1: K2CO3 / 6 h / 0 - 20 °C
9.1: OsO4; aq. NMO / acetone; tetrahydrofuran; 2-methyl-propan-2-ol / 0 - 20 °C
10.1: NaIO4 / tetrahydrofuran / 1 h / 0 °C / pH 7
11.1: Zn(OTf)2; (-)-N-Me-ephedrine; Et3N / toluene / 0.5 h / 20 °C
11.2: toluene / 0.33 h / 20 °C
12.1: NaHMDS / tetrahydrofuran; dimethylformamide / 0.5 h / -78 °C
13.1: H2; quinoline / Pd/CaCO3 / benzene / 2 h
14.1: K2OsO4; aq. NMO; citric acid / 2-methyl-propan-2-ol / 24 h / 60 °C
15.1: K2CO3; Pb(OAc)4 / CH2Cl2 / 0.33 h / 0 °C
16.1: n-BuLi / hexane; diethyl ether / 0.25 h / -78 °C
16.2: MgBr2*OEt2 / hexane; diethyl ether / 0.17 h / -78 °C
16.3: MgBr2*OEt2 / hexane; CH2Cl2; diethyl ether / 1.67 h / -78 - -15 °C
17.1: 2,6-lutidine / CH2Cl2 / 0.33 h / 0 °C
18.1: PPTS / methanol; CH2Cl2 / 2 h / 0 °C
With
1-ethyl-piperidine; 2,6-dimethylpyridine; quinoline; lead(IV) acetate; manganese(IV) oxide; potassium osmate(VI); sodium periodate; osmium(VIII) oxide; tin(II) trifluoromethanesulfonate; n-butyllithium; N-methyl-2-indolinone; iron(III)-acetylacetonate; (-)-N-methylephedrine; hydrogen; isopropylmagnesium chloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; triethylamine; citric acid; lithium hexamethyldisilazane;
Lindlar's catalyst;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
1.2: Claisen condensation;
DOI:10.1021/ja073590a