Production Method 1

824-94-2

18162-48-6

13291-18-4

1011-54-7

78-39-7

37595-74-7

1066-54-2

6638-79-5

29576-14-5

1632973-29-5

139713-80-7

Reaction Conditions

1.1R:H2, C:Pd, S:MeOH, 8 h, rt
1.2R:Diimidazolyl ketone, R:MeNHOMe-HCl, S:CH2Cl2, 3 h, rt
1.3S:THF, 0°C; 0°C → 23°C; 3 h, 23°C
2.1R:CeCl3 ?7H2O, S:MeOH, 15 min, -5°C
2.2R:NaBH4, 30 min, -5°C
2.3R:HCl, S:H2O
2.4S:EtCO2H, 24 h, reflux
3.1R:LiOH, S:H2O, S:MeOH, 3 h, rt
3.2R:Diimidazolyl ketone, S:CH2Cl2, 3 h, rt
4.1R:BuLi, S:THF, 30 min, -78°C; -78°C → -20°C; -20°C → -78°C
4.2S:THF, -78°C; 1 h, -78°C → -20°C; -20°C → -40°C
4.3R:H2O, -40°C, pH 7
5.1R:Et3N, R:HCO2H, C:195516-84-8, S:THF, 2.5 h, rt
6.1R:K2CO3, S:MeOH, 2.5 h, rt
6.2R:1H-Imidazole, S:DMF, 0°C; overnight, rt
7.1C:13465-09-3, S:CH2Cl2, 30 min, -20°C
7.2S:CH2Cl2, 4 h, -20°C
7.3R:NaHCO3, S:H2O
8.1R:BH3-THF, S:THF, 0°C; 4 h, rt; rt → 0°C
8.2R:NaOH, R:H2O2, S:H2O, 0°C; 3 h, rt
8.3R:Na2S2O3, S:H2O
9.1R:Bu4N+ ?I-, R:NaH, S:DMF, 0°C; 30 min, rt
9.2overnight, rt
9.3R:p-MeC6H4SO3H, S:MeOH, 3 h, rt
10.1R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 20 min, 0°C
10.2R:Me2CHOH
10.3R:K [N(SiMe3)2], S:THF, S:PhMe, 30 min, -78°C
10.4S:THF, -78°C; 30 min, -78°C; overnight, -78°C → rt
11.1R:DDQ, S:H2O, S:CH2Cl2, 0.5 h, rt
11.2R:Na2S2O3, S:H2O
11.3R:LiCl, R:Bu3N, C:Pd(PPh3)4, S:MeCN, 8 h, rt
12.1C:Et3SiH, C:RhCl(PPh3)3, S:PhMe, rt; 8 h, reflux
13.1R:Ce(NH4)2(NO3)6, S:H2O, S:MeCN, 1.5 h, rt
13.2R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 30 min, 0°C
13.3R:Me2CHOH
14.1R:BBr3, S:CH2Cl2, 1 h, -78°C
15.1R:NaH, S:DMF, 0°C; 30 min, rt
15.22 h, rt
16.1R:PhNMe2, 8 h, reflux
17.1R:NaHCO3, R:NaIO4, C:OsO4, S:H2O, S:t-BuOH, 12 h, rt
17.2R:Na2S2O3, S:H2O, 30 min, rt
18.1R:NaBH4, R:NH4Cl, S:H2O, S:MeOH, 30 min, 0°C
18.2R:NaIO4, S:H2O, S:MeOH, 50 min, 0°C
19.1R:Na2 EDTA, R:MeC(=O)CF3, R:NaHCO3, R:Oxone, S:H2O, S:MeCN, 5 h, 0°C
19.2R:K2CO3, R:H2O2, S:H2O, S:MeOH, 2 h, 0°C
20.1R:NaBH4, S:MeOH, 1 h, 0°C
20.2R:NH4Cl, S:H2O
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Reference

Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues

By Xu, Hongtao et al, Journal of Organic Chemistry, 2014, 79(21), 10110-10122

Triptolide Impurity 30 Raw materials

• 4-Methoxybenzylchloride
• tert-butyl(chloro)dimethylsilane
• Bromo(isopropenyl)magnesium Solution (0.5M in THF)
• (E)-3-(2-methoxyphenyl)prop-2-enoic acid
• Triethyl orthoacetate
• N,N-Bis(trifluoromethylsulfonyl)aniline
• ethynyltrimethylsilane
• N,O-Dimethylhydroxylamine hydrochloride
• trans-Crotyl bromide

Triptolide Impurity 30 Preparation Products

• 16-Hydroxytriptolide (139713-80-7)
• Triptolide Impurity 30 (1632973-29-5)

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