1: diazomethyl-phosphonic acid dimethyl ester With potassium tert-butylate in tetrahydrofuran T=-78°C; 0.0833333 h; 2: nicotine-5-carboxaldehyde in tetrahydrofuran T=-78 - 20°C; 18 h;

sodium hydride in toluene

tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 0.333333 h;

1: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 2: 92 percent / NaH / toluene / 2 h / Heating View Scheme

1: 1.) LiN(TMS)2, 2.) 6 M HCl / 1.) THF, 25 deg C, 2.) water 2: 1.) Cbz-D-proline, NaBH4, 2.) aq. HCOOH / 1.) CH2Cl2 3: 92 percent / PPh3, CuI / 10percent Pd-C / 1,2-dimethoxy-ethane; H2O 4: 97 percent / NaH / toluene View Scheme

1: 1.) Cbz-D-proline, NaBH4, 2.) aq. HCOOH / 1.) CH2Cl2 2: 92 percent / PPh3, CuI / 10percent Pd-C / 1,2-dimethoxy-ethane; H2O 3: 97 percent / NaH / toluene View Scheme

1: diethyl ether / 1 h / -100 °C 2: 100 percent / Et3N / CH2Cl2 / 0.08 h / 0 °C 3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 4: B(C6H11)2H / tetrahydrofuran 5: 94 percent / HCOOH / H2O / 3 h / 80 °C 6: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 7: 92 percent / NaH / toluene / 2 h / Heating View Scheme

1.1: (COCl)2; DMF / 1.3 h / -20 °C 1.2: 63 percent / LiAlH(O-t-Bu)3; CuI / dimethylformamide / 0.25 h 2.1: diethyl ether / 1 h / -100 °C 3.1: 100 percent / Et3N / CH2Cl2 / 0.08 h / 0 °C 4.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5.1: B(C6H11)2H / tetrahydrofuran 6.1: 94 percent / HCOOH / H2O / 3 h / 80 °C 7.1: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 8.1: 92 percent / NaH / toluene / 2 h / Heating View Scheme

1: 94 percent / HCOOH / H2O / 3 h / 80 °C 2: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 3: 92 percent / NaH / toluene / 2 h / Heating View Scheme

1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 2: (+)-diisopinocamphenylchloroborane / tetrahydrofuran / 20 h / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.08 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: B(C6H11)2H / tetrahydrofuran 6: 94 percent / HCOOH / H2O / 3 h / 80 °C 7: 83 percent / CuI; Ph3P; K2CO3 / Pd/C / 1,2-dimethoxy-ethane / 16 h / Heating 8: 92 percent / NaH / toluene / 2 h / Heating View Scheme