Multi-step reaction with 31 steps
1.1: 90 percent / aq. HCl / CHCl3 / 20 °C
2.1: CSA / CH2Cl2 / 20 °C
3.1: N-methylmorpholine / CH2Cl2 / 20 °C
4.1: 98 percent / MeI; NaHCO3 / H2O; acetonitrile / 20 °C
5.1: 95 percent / SmI2 / methanol; tetrahydrofuran / 0 °C
6.1: 2,6-lutidine / CH2Cl2 / 0 °C
7.1: DIBAH / CH2Cl2 / 0 °C
8.1: 2,6-lutidine / CH2Cl2 / -78 °C
9.1: NaI / acetone / 60 °C
10.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C
10.2: 100 percent / SiO2; H2O
11.1: TBAF / tetrahydrofuran / 20 °C
12.1: N-methylmorpholine / CH2Cl2 / 20 °C
13.1: 84 percent / SmI2 / methanol; tetrahydrofuran / 20 °C
14.1: 100 percent / DIBAH / toluene / -78 °C
15.1: 100 percent / toluene / 100 °C
16.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
17.1: 89 percent / DIBAH / toluene / -78 °C
18.1: 96 percent / (-)-DET; Ti(OiPr)4; TBHP / 4 Angstroem MS / CH2Cl2 / -35 °C
19.1: SO3*pyridine; Et3N / dimethylsulfoxide; CH2Cl2 / 20 °C
20.1: NaHMDS / tetrahydrofuran / 0 °C
21.1: 74 percent / TBAF / tetrahydrofuran / 20 °C
22.1: 68 percent / PPTS / CH2Cl2 / 0 °C
23.1: 9-BBN / tetrahydrofuran / 0 °C
23.2: 82 percent / 30percent H2O2; 3 N NaOH / tetrahydrofuran / 0 °C
24.1: 87 percent / NaH; Bu4NI / tetrahydrofuran / 0 °C
25.1: 85 percent / CSA / methanol / 20 °C
26.1: 2,6-lutidine / CH2Cl2 / -78 °C
26.2: 100 percent / CH2Cl2 / -78 °C
27.1: 100 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C
28.1: CSA / methanol / 20 °C
29.1: 2,6-lutidine / CH2Cl2 / 0 °C
30.1: 83 percent / NaIO4 / RuO2 / acetonitrile; CCl4; H2O / 20 °C
31.1: 67 percent / CSA / methanol / 80 °C
With
4-methyl-morpholine; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; pyridine-SO3 complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; lithium diisopropyl amide; methyl iodide;
ruthenium(IV) oxide; 4 Angstroem MS;
In
tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; water; dimethyl sulfoxide; acetone; toluene; acetonitrile;
3.1: hetero-Michael reaction / 12.1: hetero-Michael reaction / 15.1: Wittig reaction / 18.1: Sharpless epoxidation / 20.1: Wittig reaction;
DOI:10.1021/ol026804w