dimethylsulfide; ozone 1.) CH2Cl2, -35 deg.C, 2.) CH2Cl2, 3h, RT; Yield given. Multistep reaction;

Grubb's 2nd generation catalyst in dichloromethane T=40°C; 3 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

Grubb's 2nd generation catalyst in dichloromethane T=40°C; 3 h;

1.1: O3 / CH2Cl2 / 0.17 h / -78 °C 1.2: 93 percent / polymer-supported triphenylphosphine / CH2Cl2 / 14 h / 20 °C 2.1: 77 percent / BH3*THF / tetrahydrofuran / 0.25 h / 20 °C 3.1: 100 percent / diethylamino-polystyrene / CH2Cl2 / 2.5 h / 0 °C 4.1: 100 percent / pentane / 3.5 h / 0 °C 5.1: LDA / hexane; tetrahydrofuran / 0.17 h / -78 - -15 °C 5.2: 94 percent / hexane; tetrahydrofuran / 2 h / -78 - -40 °C View Scheme

hydrogenchloride; Schwartz's reagent; 2,2,6,6-tetramethylpiperidinyl-lithium Yield givenMultistep reaction;

1: 4-methyl-pent-1-ene With diisobutylaluminium hydride in dichloromethane 2: 4-[(tert-butyldimethylsilyl)oxy]-1-butene With isobutylaluminoxane; (-)-bis[(1-neomenthyl)indenyl]zirconium dichloride in dichloromethane 3 h; 3: With tetrabutyl ammonium fluoride in tetrahydrofuran Title compound not separated from byproducts;

ozone; triethylamine in dichloromethane T=-78 - 20°C; 2 h; Inert atmosphere;

1: Grubb's 2nd generation catalyst / dichloromethane / 3 h / 40 °C / Inert atmosphere 2: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere View Scheme