Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids
- Corresponding author: Gong Jianxian, gongjx@pku.edu.cn Yang Zhen, zyang@pku.edu.cn
Citation: Jiang Chongguo, Chen Sijia, Gong Jianxian, Yang Zhen. Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids[J]. Acta Chimica Sinica, ;2020, 78(9): 928-932. doi: 10.6023/A20060198
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Reagents and Conditions: a) Li (3.5n1), NH3(l), -40 ℃, 12 h; H2O (1.5n1), -40 ℃, 30 min, 2 (2.0n1), THF, -40 ℃, 12 h; b) KHMDS (1.5n3), THF, 0 ℃, 2 h, then HMPA (1 mL/mmol), PhSeBr (2.0n3), -78 ℃, 1 h; c) H2O2 (3.0n3), pyridine (10.0n3), THF, 0 ℃, 5 h; d) KHMDS (1.5n4), THF, 0 ℃ to 50 ℃, 2 h, then MeI (3.0n4), 0 ℃ to 25 ℃, 12 h; e) Li (3.n4), NH3(l), -40 ℃, 12 h. KHMDS=Potassium bis(trimethylsilyl)amide, HMPA=Hexamethylphosphoramide.
Reagents and Conditions: a) EtOCH2Cl (2.0n6), i-Pr2NEt (3.0n6), THF, 25 ℃, 12 h; b) O3, DCM, -78 ℃, then Me2S (3.5n7), -78 ℃, 1 h; c) 9 (6.0n8), THF, -78 ℃, 3 h.
Reagents and Conditions: a) BnMgBr (6.0n8), THF, -78 ℃, 3 h; b) PhMgBr (6.0n8), THF, -78 ℃, 3 h.
Reagents and Conditions: a) t-BuOK (3.0n10), THF, 60 ℃, 10 h; b) CSA (0.1n17), THF, 60 ℃, 10 h. CSA=Camphorsulfonic acid.