tributylphosphine; water in tetrahydrofuran T=20°C; 9 h; Inert atmosphere;

1: 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: benzylidene-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)benzyl]amine in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; optical yield given as percent de;

1: 6-methoxy-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-benzyl-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: 2,3,4,5-tetrahydropyridine in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; optical yield given as percent dediastereoselective reaction;

1: 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: benzyl-pyridin-3-ylmethylene-amine in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; optical yield given as percent dediastereoselective reaction;

1: 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: N-(furan-2-ylmethylene)benzylamine in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; optical yield given as percent dediastereoselective reaction;

hydrogenchloride; iodine; dimethyl sulfoxide Oxidation; 1.16667 h; Heating;

1: 5-bromo-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: Isopropyl(H)=NBn in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; diastereoselective reaction;

sodium hydroxide in methanol Hydroformylation; Oxidative dimerization; 3 h; Heating;

sodium hydroxide; dihydrogen peroxide in 1,4-dioxane T=44 - 48°C; Hydrolysis; Oxidation; 3 h;

trisodium phosphorothioate in methanol Substitution; Oxidative dimerization; 72 h; Heating;