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ChemicalBook CAS DataBase List cularine
479-39-0

cularine synthesis

6synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 12 steps
1: Br2 / acetic acid / 2 h / 25 °C
2: K2CO3 / ethanol / 2 h / 75 °C
3: AcONH4; AcOH / 3 h / 80 °C
4: 72 percent / LAH / tetrahydrofuran / 8 h / 70 °C
5: 79 percent / CCl4 / CH2Cl2 / 72 h / 40 °C
6: 95 percent / sodium amide / toluene / 1 h / 100 °C
7: 76 percent / toluene / 14 h / 75 °C
8: 92 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -10 - 5 °C
9: 83 percent / TFMSA / 3 h / 60 °C
10: 87 percent / NaH; C6F5I(OCOCF3)2 / toluene / 2 h / -10 °C
11: methanol / 10 h
12: 34.52 mg / sodium borohydride / methanol / 0 - 20 °C

References:

Rodrigues, J. Augusto R.;Abramovitch, Rudolph A.;De Sousa, Joana D. F.;Leiva, Genaro C. [Journal of Organic Chemistry,2004,vol. 69,# 9,p. 2920 - 2928]

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