Technology Process of Benzoic acid 4-iodo-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-butyl ester
There total 13 articles about Benzoic acid 4-iodo-2-((1S,3aS,6aS)-3a-methyl-6-methylene-1,3a,4,5,6,6a-hexahydro-pentalen-1-yl)-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium iodide;
In
acetone;
for 24h;
Ambient temperature;
DOI:10.1021/ja9609359
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 95 percent / TMSOTf / CH2Cl2 / 40 h / -78 °C
2: NaBH4 / methanol / 1 h / 0 - 20 °C
3: DMAP, pyridine / 42 h / Ambient temperature
4: DBU / toluene / 40 h / Heating
5: 94 percent / TsOH*H2O / acetone / 48 h / Ambient temperature
6: 71 percent / LDA / tetrahydrofuran / -78 - 20 °C
7:
2, (S)-BINAP, NaBr / dimethylsulfoxide / 1 h / Ambient temperature8: 84 percent / aq. LiCl / dimethylsulfoxide / 6 h / Heating
9: 96 percent / DIBALH / CH2Cl2; hexane / -78 - 0 °C
10: 100 percent / pyridine, DMAP / CH2Cl2 / 16 h / Ambient temperature
11: 97 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature
12: 100 percent / Et3N / CH2Cl2 / 1 h / -23 - 0 °C
13: 100 percent / NaI / acetone / 24 h / Ambient temperature
With
pyridine; dmap; sodium tetrahydroborate; bis(η3-allyl-μ-chloropalladium(II)); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; sodium iodide; sodium bromide; lithium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetone; toluene;
DOI:10.1021/ja9609359
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 71 percent / LDA / tetrahydrofuran / -78 - 20 °C
2:
2, (S)-BINAP, NaBr / dimethylsulfoxide / 1 h / Ambient temperature3: 84 percent / aq. LiCl / dimethylsulfoxide / 6 h / Heating
4: 96 percent / DIBALH / CH2Cl2; hexane / -78 - 0 °C
5: 100 percent / pyridine, DMAP / CH2Cl2 / 16 h / Ambient temperature
6: 97 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature
7: 100 percent / Et3N / CH2Cl2 / 1 h / -23 - 0 °C
8: 100 percent / NaI / acetone / 24 h / Ambient temperature
With
pyridine; dmap; bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl ammonium fluoride; diisobutylaluminium hydride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; sodium iodide; sodium bromide; lithium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1021/ja9609359
