ChemicalBook CAS DataBase List Ambruticin

Ambruticin synthesis

15synthesis methods

Product Name:Ambruticin
CAS Number:58857-02-6
Molecular formula:C28H42O6
Molecular Weight:474.634

2H-Pyran-2-carboxaldehyde, 6-ethyl-3,6-dihydro-5-methyl-, (2R,6R)- (9CI)

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Yield:-

Steps:

Multi-step reaction with 13 steps
1.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C
2.1: Bu₃SnCu(Bu)CNLi₂ / tetrahydrofuran; hexane / 0.25 h / -78 °C
2.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C
2.3: 80 percent / I₂ / diethyl ether / 0 - 20 °C
3.1: 88 percent / Pd(PPh₃)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C
4.1: H₂; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr
5.1: 190 mg / CrCl₂ / tetrahydrofuran / 20 °C
6.1: 96 percent / Pd(OAc)2; Ag₂CO₃; Et₃N / CH₂Cl₂ / 24 h / 20 °C
7.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C
8.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH₂Cl₂ / 2 h / -10 °C
9.1: PPh₃; DEAD / tetrahydrofuran / 3 h / 20 °C
10.1: 93 mg / ammonium molybdate; aq. H₂O₂ / ethanol; tetrahydrofuran / 20 °C
11.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C
12.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
13.1: 87 percent / O₂; NaHCO₃ / Pt / H₂O; acetone; propan-2-ol / 50 °C