Multi-step reaction with 9 steps
1.1: Cp2ZrCl2 / hexane; 1,2-dichloro-ethane / 40 °C
1.2: 86 percent / I2 / tetrahydrofuran; hexane; 1,2-dichloro-ethane / 0.5 h / -30 - 0 °C
2.1: 62 percent / PdCl2(CH3CN)2 / dimethylformamide / 72 h / 20 °C
3.1: 80 percent / t-BuOOH; Ti(OiPr)4; L-(+)-DIPT / CH2Cl2; 2,2,4-trimethyl-pentane / 36 h / -24 °C
4.1: tetra-n-propylammonium perruthenate; NMO; 4 Angstroem molecular sieves / acetonitrile; CH2Cl2 / 0.67 h
5.1: KHMDS / toluene; tetrahydrofuran / 2 h
6.1: tetrahydrofuran / 0.75 h
6.2: CAN / acetonitrile / 5 h / 0 - 20 °C
7.1: 57 percent / MCPBA; K2CO3 / CH2Cl2 / 0.5 h
8.1: O3 / CH2Cl2 / 0.03 h / -78 °C
8.2: 18 percent / NaBH4/Al2O3 / benzene / 14 h / 20 °C
9.1: 40 percent / SmI2 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.08 h
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; zirconocene dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; potassium hexamethylsilazane; potassium carbonate; ozone; 3-chloro-benzenecarboperoxoic acid;
dichloro bis(acetonitrile) palladium(II);
In
tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
1.1: Addition / 1.2: Iodination / 2.1: Stille coupling / 3.1: Epoxidation / 4.1: Oxidation / 5.1: Wittig methylenation / 6.1: Carbonylation / 6.2: Oxidation / 7.1: Epoxidation / 8.1: Oxidation / 8.2: Reduction / 9.1: Elimination;