2-C4b E-1-Chlor-37-dimethyl-2 6-octadien aus Nerol 1)MeSO2CI 2)Pyrid OH -Me Me gute Abgangsgruppe 2-DI (S)-()-2-Brom-3-hydroxypropionsaure aus L-Serin 2-D2 Kalium-(R)-2, 3-epoxy propionat aus(S)-(-)-2-Brom 3-hydroxy-propionsaure(2-D1) 2-D3 R-Glycidsaurebenzylester aus Kalium-(R)-23 3 epoxypropionat(2-D2
2-C4b E-1-Chlor-3,7-dimethyl-2,6-octadien aus Nerol Cl 1) MeSO2Cl OH 2) Pyridin OH Me S Cl O O OH S O O Me Cl O S Me O O Cl Cl O S Me O O gute Abgangsgruppe 2-D1 (S)-(-)-2-Brom-3-hydroxypropionsäure aus L-Serin 2-D2 Kalium-(R)-2,3-epoxypropionat aus (S)-(-)-2-Brom- 3-hydroxy-propionsäure (2-D1) 2-D3 R-Glycidsäurebenzylester aus Kalium-(R)-2,3- epoxypropionat (2-D2)
HBr, NaNO2 2-D1 KOH EtoH 2-D2 CBHs CH2Br Dibenzo-18-krone-6 CO2 CH2Ph (2D4) 2-D3 2-D1 HO OH S. 2-El OH HO 2 mal Inversion Rentention 2KOH COH -2H2O CO2 CH2 KB 2-D3
2-D2 2-D3 CO2 HO NH3 HBr, NaNO2 CO2H HO Br K O CO2 O CO2CH2Ph C6H5CH2Br CH3CN, Dibenzo-18-krone-6 (2-D4) 2-D1 KOH EtOH HO C NH3 OH O HO CO2H Br 2 mal Inversion Rentention 2-D1 K O CO2 Br O CO2CH2 Ph KBr CO2H HO Br 2KOH CO2 O Br -2H2O K K -KBr SN2 2-D2 2-D3 HO C N2 OH O HO O OH - N2 s. 2-E1
2-D4 Dibenzo-18-krone-6 aus Brenzcatechin und bis(2 chlorethyl)ether OH NaOH.△ OH CI Cl n-Butanol 2-D4 O Templateffekt 2-El(S)-2-Chlorpropionsaure aus L-Alanin 2-E2(R)-2-(Pyrrolidin-l-yDpropionsaure aus(S)-2 Chlorpropionsaure(2-El) O2C、CH3NaNO2/HC O2C、CH 2-E1 NH O2C. (2-E1) 2-E2 HO-N N=O
2-D4 Dibenzo-18-krone-6 aus Brenzcatechin und Bis(2- chlorethyl)ether 2-D4 OH OH O O O O O O O NaOH,∆ Cl Cl + n-Butanol OH OH OH O O Cl Cl OH O O Cl -Cl O O O O O O +OH -H2O Na Templateffekt 2-E1(S)-2-Chlorpropionsäure aus L-Alanin 2-E2(R)-2-(Pyrrolidin-1-yl)propionsäure aus (S)-2- Chlorpropionsäure (2-E1) 2-E1 2-E2 O2C CH3 Cl O2C CH3 NH3 O2C CH3 Cl O2C CH3 N NH NaNO2 / HCl (2-E1) HO N O + H H2O N O N O N O H
o2C、CH3 HOoC、CH3 HooC、CH3 NH2 O NH2 HooC、CH3 HooC、CH3 HooC、CH3 ONH NH N AOH2 OH CH3 ACH3 C○ O2C N一H O2C\ CH3 2-E2 2-E1
O2C CH3 NH3 HOOC CH3 NH2 N O HOOC CH3 NH2 N O ~ H HOOC CH3 NH N OH HOOC CH3 NH N OH ~ H HOOC CH3 N N OH2 CH3 N N O OH O HO CH3 H O HO CH3 H Cl O2C CH3 Cl - H 2-E1 NH SN2 2-E2 O2C CH3 N H
2-E3 1, 4-Diiodbutan aus Tetrahydrofuran KI, H3PO -H,O mit H3 PO4 Polyphosphate 2-E4 S-2-(Pyrrolidin-1-yDpropionsaure aus L-Alanin und 1, 4- Diodbutan(2-E3) CH3 H3 Nahco,/ Toluol 2-E4 O2C、∠CH3 +OH HO NHn O2C、CH3 2 O2C、CH3
2-E3 1,4-Diiodbutan aus Tetrahydrofuran 2-E3 O I I KI, H3PO4, ∆ O H O H I I OH H I OH2 I -H2O I I * *mit H3PO4 Polyphosphate 2-E4 S-2-(Pyrrolidin-1-yl)propionsäure aus L-Alanin und 1,4- Diodbutan (2-E3) 2-E4 O2C CH3 NH3 O2C CH3 N NaHCO3 / Toluol I I (2-E3) O2C CH3 NH3 +OH -H2O O2C CH3 NH2 I I -I O2C CH3 HN SN2 I SN2 -I O2C CH3 N H H