C10H16O4S in diethyl ether T=0°C; 1.5 h;

1: 85 percent / BH3*DMS / tetrahydrofuran / 24 h / 20 °C 2: 93 percent / (1R)-(+)-α-pinene / diethyl ether / 1.5 h / 0 °C View Scheme

1: With dimethylsulfide borane complex in tetrahydrofuran Addition; 3 h; 2: (+)-(1R,5R)-α-pinene in tetrahydrofuran T=0°C; Addition; 96 h; 3: methanol in tetrahydrofuran T=0°C; Substitution; 1 h;

1: (-)-Ipc2BOMe; 2-propenylmagnesium bromide in diethyl ether T=0°C; 1 h; Inert atmosphere; 2: 4-azidobutyraldehyde in diethyl ether T=-78°C; Brown allylboration; 3 h; Inert atmosphere; 3: With dihydrogen peroxide; sodium hydroxide in methanol; diethyl ether; water optical yield given as percent eeenantioselective reaction;

1: (-)-Ipc2BOMe; 2-propenylmagnesium bromide in diethyl ether; hexane T=0 - 20°C; 1 h; 2: 2-((4R,5R)-5-((tert-butyldimethylsilanyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde in diethyl ether; hexane T=-78 - 0°C; 1 h; 3: With dihydrogen peroxide; sodium hydroxide in diethyl ether; hexane; water 8 h; diastereoselective reaction;