ChemicalBook CAS DataBase List Apratoxin A

Apratoxin A synthesis

9synthesis methods

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)

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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]

1,2-Pyrrolidinedicarboxylic acid, 2-[(1S,3R,5S,6S)-6-carboxy-1-(1,1-dimethylethyl)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylheptyl] 1-(1,1-dimethylethyl) ester, (2S)-

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References

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References

2H-Pyran-2-one, 6-(1,1-dimethylethyl)tetrahydro-4-methyl-, (4R,6S)-

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References

1,5-Heptanediol, 3,6,6-trimethyl-, (3S,5S)-

531559-37-2
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References