Stereocontrolled total synthesis of (+/-)-gelsemine

被引：21
|
作者：
Fukuyama, T [1 ]
Liu, G [1 ]
机构：
[1] RICE UNIV,DEPT CHEM,HOUSTON,TX 77005
来源：
PURE AND APPLIED CHEMISTRY | 1997年 / 69卷 / 03期
关键词：
D O I：
10.1351/pac199769030501
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The stereocontrolled total synthesis of gelsemine (1) via 21-oxogelsemine (2) is reported. Our total synthesis features a stereoselective condensation of cyclopropyl carboxaldehyde 11 and 4-iodo-oxindole, a facile construction of the bicyclo[3.2.1] intermediate 20 with a complete control of the stereochemistry by means of a novel application of divinylcyclopropane-cycloheptadiene rearrangement, and an unprecedented silver ion-mediated lactam formation between carbamoyl chloride and enecarbamate.
引用
收藏
页码：501 / 505
页数：5
相关论文
共 50 条
  • [1] STEREOCONTROLLED TOTAL SYNTHESIS OF +/--GELSEMINE
    LIU, G
    FUKUYAMA, T
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 292 - ORGN
  • [2] Stereocontrolled total synthesis of (+/-)-gelsemine
    Fukuyama, T
    Liu, G
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) : 7426 - 7427
  • [3] Stereocontrolled total synthesis of (&plusmn)-gelsemine
    Fukuyama, Tohru
    Liu, Gang
    Journal of the American Chemical Society, 1996, 118 (31):
  • [4] THE TOTAL SYNTHESIS OF (+/-)-GELSEMINE
    NEWCOMBE, NJ
    YA, F
    VIJN, RJ
    HIEMSTRA, H
    SPECKAMP, WN
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) : 767 - 768
  • [5] Total synthesis of (±)-gelsemine
    Madin, A
    O'Donnell, CJ
    Oh, TB
    Old, DW
    Overman, LE
    Sharp, MJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (19) : 2934 - 2936
  • [6] Biomimetic Total Synthesis of (+)-Gelsemine
    Zhou, Xuan
    Xiao, Tao
    Iwama, Yusuke
    Qin, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4909 - 4912
  • [7] STUDIES ON THE TOTAL SYNTHESIS OF GELSEMINE
    OH, T
    OVERMAN, LE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 135 - ORGN
  • [8] Total synthesis of gelsemine.
    O'Donnell, CJ
    Earley, WG
    Jacobsen, JE
    Madin, A
    Oh, T
    Old, DW
    Overman, LE
    Sharp, MJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U75 - U75
  • [9] Advances in the Total Synthesis of Gelsemine
    Yang, Liyan
    Wang, Zhonglei
    CURRENT ORGANIC CHEMISTRY, 2022, 26 (04) : 356 - 368
  • [10] A TOTAL SYNTHESIS OF GELSEMINE - OXINDOLE SPIROANNELATION
    DUTTON, JK
    STEEL, RW
    TASKER, AS
    POPSAVIN, V
    JOHNSON, AP
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) : 765 - 766
12345