Stereocontrolled total synthesis of pancratistatin

被引:75
|
作者
Kim, S
Ko, H
Kim, E
Kim, D
机构
[1] Seoul Natl Univ, Inst Nat Prod Res, Seoul 110460, South Korea
[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
关键词
D O I
10.1021/ol0256419
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new total synthesis of the antitumor alkaloids, pancratistatin (1), has been accomplished from readily available staring materials. The Claisen rearrangement of dihydropyranethylene 5 was employed to construct the A and C rings. Stereo- and regiocontrolled functional group interchange, such as iodolactonization, dihydroxylations, and a cyclic sulfate elimination reaction, allows for the production of the target natural product.
引用
收藏
页码:1343 / 1345
页数:3
相关论文
共 50 条
  • [1] Total synthesis of pancratistatin
    Rastogi, Shiva K.
    Nadein, Oleg N.
    Kornienko, Alexander
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3045 - U3045
  • [2] TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN
    DANISHEFSKY, S
    LEE, JY
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) : 4829 - 4837
  • [3] A STEREOCONTROLLED APPROACH TO PANCRATISTATIN
    THOMPSON, RC
    KALLMERTEN, J
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 234 - ORGN
  • [4] ASYMMETRIC TOTAL SYNTHESIS OF (+)-PANCRATISTATIN
    TROST, BM
    PULLEY, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (40) : 10143 - 10144
  • [5] Studies towards the total synthesis of pancratistatin.
    Nadein, ON
    Kireev, AS
    Kornienko, A
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U80 - U80
  • [6] Stereocontrolled total synthesis of (-)-kaitocephalin
    Vaswani, Rishi G.
    Chamberlin, A. Richard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05): : 1661 - 1681
  • [7] A stereocontrolled total synthesis of (±)-saframycin A
    Kimura, Shinya
    Saito, Naoki
    [J]. TETRAHEDRON, 2018, 74 (34) : 4504 - 4514
  • [8] A STEREOCONTROLLED TOTAL SYNTHESIS OF ZOAPATANOL
    NICOLAOU, KC
    CLAREMON, DA
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 244 - ORGN
  • [9] STEREOCONTROLLED TOTAL SYNTHESIS OF (-)-MAYTANSINOL
    KITAMURA, M
    ISOBE, M
    ICHIKAWA, Y
    GOTO, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) : 3252 - 3257
  • [10] STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-QUINOCARCIN
    FUKUYAMA, T
    NUNES, JJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5196 - 5198