1: 79 percent / sodium methylsulfinyl carbanion / dimethylsulfoxide / 10 °C 3: 94 percent / imidazole / dimethylformamide / 4 h / 25 °C 4: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 5: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 6: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 7: 25 °C / saponification View Scheme

1: 79 percent / sodium methylsulfinyl carbanion / dimethylsulfoxide / 10 °C 3: 94 percent / imidazole / dimethylformamide / 4 h / 25 °C 4: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 5: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 6: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 7: 25 °C / saponification View Scheme

1: 94 percent / imidazole / dimethylformamide / 4 h / 25 °C 2: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 3: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 4: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 5: 25 °C / saponification View Scheme

1: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 2: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 4: 25 °C / saponification View Scheme

1: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 2: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 4: 25 °C / saponification View Scheme

1: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 2: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 3: 25 °C / saponification View Scheme

2: 94 percent / imidazole / dimethylformamide / 4 h / 25 °C 3: 1.) n-butyllithium, 2.) Gilman reagent, cuprrous cyanide, HMPA 4: H2, triethylamine / Lindlar catalyst / hexane / 760 Torr 5: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 6: 25 °C / saponification View Scheme

1: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C 2: 25 °C / saponification View Scheme

T=25°C; saponification;

crude enzyme of Ulva conglobata; phosphorous acid trimethyl ester