苯丙素苷Acteoside, Isoacteoside和Ligupurpuroside J的全合成

胡志飞, 徐鹏, 魏炳成, 俞飚

Total Synthesis of Phenylpropanoid Glycosides, Acteoside, Isoacteoside and Ligupurpuroside J†

HU Zhifei, XU Peng, WEI Bingcheng, YU Biao

Table 1 Regioselective glycosylation of acceptor 9 with donors 7, 12 and 13a

Entry Donor Catalyst Amount(%, mass fraction) Solvent Temp./℃ Product Yield(%) or molar ratio 1 7 PPh3AuNTf2 10 DCM -70 16a 13b 2 7 PPh3AuNTf2 10 DCM -50 16a, 16b, 16c, 16d 51b, 19b, Trace, 10b 3 7 PPh3AuNTf2 10 DCM -30 16a, 16b 16a/16b=1.5—2:1c 4 7 PPh3AuNTf2 10 Toluene -50 16a, 16b 16a/16b=1:1.5—2c 5 7 PPh3AuNTf2 10 Ether -50 16a, 16b 16a/16b=1:1.5—2c 6 7 PPh3AuOTf 10 DCM -50 16a, 16b 16a/16b=1.2—1.5:1c 7 12 TMSOTf 5—20 DCM -50 16a, 16b, 16c, 16d 29d, 24d, 10d, 7d 8 13 TMSOTf/NIS 120/20 DCM -50 16a, 16b, 16c, 16d 28d, 21d, 14d, 6d 9 7 TMSOTf/NIS 120/10 DCM -50 16a, 16b, 16c, 16d 26d, 22d, 8d, 28d