WORTMANNIN synthesis
- Product Name:WORTMANNIN
- CAS Number:19545-26-7
- Molecular formula:C23H24O8
- Molecular Weight:428.43
22614-34-2
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19545-26-7
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Yield:-
Steps:
Multi-step reaction with 28 steps
1: iPr2NEt / CH2Cl2 / 0.5 h / -78 °C
2: 1) mCPBA, KHCO3, 2) citric acid / 1) CH2Cl2, -30 to -20 deg C, 1 h, 2) MeOH, 0 deg C to RT
3: NaIO4 / methanol; H2O / 0 deg C, 12 h; RT, 3 h
4: CHCl3 / Ambient temperature
5: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h
6: 89 percent / nBu3P / tetrahydrofuran / 1 h / 0 - 20 °C
7: 85 percent / 30percent H2O2 / tetrahydrofuran / 18 h / 0 - 20 °C
8: I2, NaHCO3 / CH2Cl2 / 48 h / Ambient temperature
9: 90 percent / methanol / 4 h / 0 - 20 °C
10: LTBA / tetrahydrofuran / 3 h / 0 °C
11: pyridine / 2 h / 0 - 20 °C
12: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating
13: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h
14: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C
15: DDQ / dioxane / 4 h / 80 °C
16: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature
17: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature
18: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C
19: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature
20: CH(NMe2)3 / 1 h / 100 °C
21: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature
22: PCC / CH2Cl2 / 5 h / Ambient temperature
23: CH2Cl2 / 0.33 h / Ambient temperature
24: DBN / CH2Cl2 / 6 h / Ambient temperature
25: K2CO3, MeOH / 5 h / Ambient temperature
26: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature
27: 49 percent / pyridine / 12 h / -20 °C
28: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature
References:
Sato, Seiji;Nakada, Masahisa;Shibasaki, Masakatsu [Tetrahedron Letters,1996,vol. 37,# 34,p. 6141 - 6144]
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19545-26-7
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