Technology Process of Benzoic acid (Z)-(1R,2R,3S,7R,8R,9R)-9,13-dimethyl-4-oxo-3-phenylsulfanylmethyl-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,12-dien-9-yl ester
There total 19 articles about Benzoic acid (Z)-(1R,2R,3S,7R,8R,9R)-9,13-dimethyl-4-oxo-3-phenylsulfanylmethyl-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,12-dien-9-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
silver tetrafluoroborate;
In
dichloromethane;
at -65 ℃;
DOI:10.1021/ja011285y
- Guidance literature:
-
Multi-step reaction with 16 steps
1: Dibal-H / CH2Cl2 / -78 °C
2: Et3N / CH2Cl2 / -78 - 20 °C
3: BF3*OEt2 / CH2Cl2 / -78 - 20 °C
4: 86 percent / O2; PdCl2; aq. CuCl / dimethylformamide
5: 87 percent / CeCl3 / tetrahydrofuran
6: 91 percent / H3O+ / methanol
7: aq. LiOH / tetrahydrofuran; methanol / -30 - 0 °C
8: Cl3C6H2COCl; Et3N; DMAP / toluene
9: 61 percent / py / tetrahydrofuran / -50 - 20 °C
10: 76 percent / p-cymene / 1.5 h / 140 °C
11: 88 percent / NaBF4 / tetrahydrofuran
12: 91 percent / KH / tetrahydrofuran
13: TBAF / tetrahydrofuran
14: TPAP; NMO; 4A MS / CH2Cl2
15: LHMDS / tetrahydrofuran
16: AgBF4 / CH2Cl2 / -65 °C
With
pyridine; dmap; lithium hydroxide; silver tetrafluoroborate; sodium tetrafluoroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4-methylisopropylbenzene; boron trifluoride diethyl etherate; oxonium; tetrabutyl ammonium fluoride; oxygen; potassium hydride; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
4: Wacker oxidation / 8: Yonemitsu/Yamaguchi protocol / 10: Claisen rearrangement;
DOI:10.1021/ja011285y
- Guidance literature:
-
Multi-step reaction with 15 steps
1: Et3N / CH2Cl2 / -78 - 20 °C
2: BF3*OEt2 / CH2Cl2 / -78 - 20 °C
3: 86 percent / O2; PdCl2; aq. CuCl / dimethylformamide
4: 87 percent / CeCl3 / tetrahydrofuran
5: 91 percent / H3O+ / methanol
6: aq. LiOH / tetrahydrofuran; methanol / -30 - 0 °C
7: Cl3C6H2COCl; Et3N; DMAP / toluene
8: 61 percent / py / tetrahydrofuran / -50 - 20 °C
9: 76 percent / p-cymene / 1.5 h / 140 °C
10: 88 percent / NaBF4 / tetrahydrofuran
11: 91 percent / KH / tetrahydrofuran
12: TBAF / tetrahydrofuran
13: TPAP; NMO; 4A MS / CH2Cl2
14: LHMDS / tetrahydrofuran
15: AgBF4 / CH2Cl2 / -65 °C
With
pyridine; dmap; lithium hydroxide; silver tetrafluoroborate; sodium tetrafluoroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4-methylisopropylbenzene; boron trifluoride diethyl etherate; oxonium; tetrabutyl ammonium fluoride; oxygen; potassium hydride; triethylamine; copper(l) chloride; palladium dichloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
3: Wacker oxidation / 7: Yonemitsu/Yamaguchi protocol / 9: Claisen rearrangement;
DOI:10.1021/ja011285y
