ChemicalBook CAS DataBase List Vindoline

Vindoline synthesis

13synthesis methods

Product Name:Vindoline
CAS Number:2182-14-1
Molecular formula:C25H32N2O6
Molecular Weight:456.53

Hydrazinecarboxamide, N-[2-(6-methoxy-1-methyl-1H-indol-3-yl)ethyl]-

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Yield:-

Steps:

Multi-step reaction with 12 steps
1.1: 61 percent / EDCI; DMAP / CH₂Cl₂ / 19 h / 25 °C
2.1: 67 percent / p-toluenesulfonyl chloride; Et₃N / CH₂Cl₂ / 20 h / 25 °C
3.1: 96 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 0 - 25 °C
4.1: 53 percent / various solvent(s) / 90 h / 230 °C
5.1: Chiracel OD / propan-2-ol; hexane
6.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C
6.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C
7.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C
8.1: 91 percent / Raney-Ni; H₂ / tetrahydrofuran / 15 h / 20 °C
9.1: 97 percent / NaOAc / 17 h / 20 °C
10.1: 98 percent / H₂ / PtO₂ / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr
11.1: 89 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C
12.1: 75 percent / DEAD; PPh₃ / tetrahydrofuran / 24 h / 20 °C

References:

Choi, Younggi;Ishikawa, Hayato;Velcicky, Juraj;Elliott, Gregory I.;Miller, Michael M.;Boger, Dale L. [Organic Letters,2005,vol. 7,# 20,p. 4539 - 4542]