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N-formyl-L-leucine
4-<(4Z,7Z)-2-hydroxytrideca-4,7-dienyl>-3-hexyloxetan-2-one
(-)-lipstatin
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1.5h; 0 deg C to RT; | 50% |
(Z)-non-3-en-1-ol
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 2: 100 percent / acetonitrile / 48 h / Heating 3: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 4: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 5: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 6: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 7: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 8: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(Z)-3-nonenal
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 2: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 3: 100 percent / acetonitrile / 48 h / Heating 4: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 5: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 6: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 7: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 8: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 9: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(3Z)-1-bromo-3-nonene
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 100 percent / acetonitrile / 48 h / Heating 2: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 3: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 4: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 5: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 6: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 7: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(Z)-3-nonenal diisopropyl acetal
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating 2: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 3: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 4: 100 percent / acetonitrile / 48 h / Heating 5: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 6: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 7: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 8: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 9: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 10: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
[(3Z)-3-nonen-1-yl]triphenylphosphonium bromide
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 2: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 3: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 4: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 6: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
hexanal
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 100 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 2: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating 3: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 4: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 5: 100 percent / acetonitrile / 48 h / Heating 6: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 7: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 8: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 9: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 10: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 11: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(R)-(Z,Z)-3-<(tert-Butyldimethylsilyl)oxy>-5,8-tetradecadienal
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 2: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 3: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 4: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
Methyl (R)-(Z,Z)-3-<(tert-butyldimethylsilyl)oxy>-5,8-tetradecadienoate
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 2: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 3: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 5: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 2: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(-)-lipstatin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 2: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 3: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme |
(-)-lipstatin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine cobalt; copper(l) chloride In acetonitrile at 15℃; Temperature; Reagent/catalyst; Inert atmosphere; | 95.2% |
carbon palladium In ethanol |
(-)-lipstatin
Conditions | Yield |
---|---|
Stage #1: (-)-lipstatin With pyrographite In methanol; H20 for 0.5h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 3677.86 Torr; for 8h; | |
Stage #1: (-)-lipstatin With pyrographite In H20; isopropyl alcohol for 0.5h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 2942.29 Torr; for 6h; | |
Stage #1: (-)-lipstatin With pyrographite In H20; ethanol for 0.5h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 2206.72 Torr; for 5h; |
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