![](/CAS/20211123/GIF/350791-64-9.gif)
Apratoxin A synthesis
- Product Name:Apratoxin A
- CAS Number:350791-64-9
- Molecular formula:C45H69N5O8S
- Molecular Weight:840.13
![2-Hexanone, 4-hydroxy-5,5-dimethyl-, (4S)- (9CI)](/CAS/GIF/197454-20-9.gif)
197454-20-9
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Yield:-
Steps:
Multi-step reaction with 28 steps
1.1: 15 g / imidazole / dimethylformamide / 24 h
2.1: NaBH4 / methanol / 0.5 h
3.1: Et3N / CH2Cl2 / 2 h / 0 °C
4.1: 10 g / tBuOK / toluene / 1 h / Heating
5.1: ozone / CH2Cl2 / -78 - 20 °C
5.2: Me2S / CH2Cl2 / 24 h / 40 °C
6.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.33 h / -78 °C
6.2: hexane; tetrahydrofuran / 1 h
7.1: aq. HF / acetonitrile / 20 °C
8.1: 1.75 g / Et3N; MsCl / CH2Cl2 / 2 h
9.1: 94 percent / CuCN / diethyl ether; diethyl ether / 1 h
10.1: LiAlH4 / tetrahydrofuran / 1 h / Heating
11.1: pyridine / CH2Cl2
12.1: K2CO3 / methanol; H2O / 5 h
13.1: 2.3 g / Dess-Martin reagent / CH2Cl2 / 3 h
14.1: CF3SO3H; Et3B; DIPEA / hexane; CH2Cl2 / 0.5 h / -10 °C
14.2: 90 percent / TiCl4 / hexane; CH2Cl2 / 2 h
15.1: LiAlH4 / tetrahydrofuran / 0.5 h / Heating
16.1: 1.05 g / PPTs / 24 h
17.1: 90 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene
18.1: TsOH / methanol
19.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO3 / NaClO / CH2Cl2; H2O / 1 h
20.1: 155 mg / NaClO2; NaH2PO4 / H2O; 2-methyl-propan-2-ol; various solvent(s) / 1 h
21.1: 237 mg / HATU; DIPEA / CH2Cl2 / 12 h / 20 °C
22.1: 81 percent / DIPEA / CH2Cl2 / 1.5 h
23.1: 92 percent / trifluoromethanesulfonic anhydride; triphenylphosphine oxide / CH2Cl2 / 1 h / 0 °C
24.1: TMSOTf / CH2Cl2 / 1 h
25.1: 38 mg / HATU; DIPEA / CH2Cl2 / 20 °C
26.1: tetrabutylammonium fluoride / tetrahydrofuran
27.1: 10 mg / HATU; DIPEA / CH2Cl2 / 72 h / 20 °C
28.1: 7 mg / KCN / ethanol / 50 °C
References:
Dawei, Ma;Zou, Bin;Cai, Guorong;Hu, Xiaoyi;Liu, Jun O. [Chemistry - A European Journal,2006,vol. 12,# 29,p. 7615 - 7626]
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![Apratoxin A](/CAS/20211123/GIF/350791-64-9.gif)
350791-64-9
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