WORTMANNIN synthesis

6synthesis methods

Product Name:WORTMANNIN
CAS Number:19545-26-7
Molecular formula:C23H24O8
Molecular Weight:428.43

Androst-4-ene-3,17-dione, 9,11-epoxy-, (11α)-

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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