Total synthesis of (-)-aspidospermine via diastereoselective ring-closing olefin metathesis

被引：53
|
作者：
Fukuda, Y [1 ]
Shindo, M [1 ]
Shishido, K [1 ]
机构：
[1] Univ Tokushima, Inst Med Resources, Tokushima 7708505, Japan
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 05期
关键词：
D O I：
10.1021/ol034020s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An enantiocontrolled total synthesis of (-)-aspidospermine has been achieved. The key element of the strategy is the diastereoselective construction of the quaternary stereogenic center employing 1,4-asymmetric induction during the ring-closing olefin metathesis.
引用
收藏
页码：749 / 751
页数：3
相关论文
共 50 条
  • [1] A stereoselective synthesis of (+)-malyngolide via a ring-closing olefin metathesis
    Carda, M
    Castillo, E
    Rodríguez, S
    Marco, JA
    [J]. TETRAHEDRON LETTERS, 2000, 41 (29) : 5511 - 5513
  • [2] Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans
    Schmidt, B
    Wildemann, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18): : 5817 - 5822
  • [3] Total synthesis of (-)- and (±)-frontalin via ring-closing metathesis
    Scholl, M
    Grubbs, RH
    [J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1425 - 1428
  • [4] Ring-closing olefin metathesis
    不详
    [J]. NACHRICHTEN AUS CHEMIE TECHNIK UND LABORATORIUM, 1995, 43 (7-8): : 809 - +
  • [5] Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis
    McReynolds, MD
    Dougherty, JM
    Hanson, PR
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2239 - 2258
  • [6] Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis
    Neipp, CE
    Martin, SF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 8867 - 8878
  • [7] Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesis
    Goldring, WPD
    Hodder, AS
    Weiler, L
    [J]. TETRAHEDRON LETTERS, 1998, 39 (28) : 4955 - 4958
  • [8] Formation of macrocycles via ring-closing olefin metathesis
    [J]. Grubbs, R.H. (rhg@its.caltech.edu), 1600, American Chemical Society (66):
  • [9] Formation of macrocycles via ring-closing olefin metathesis
    Lee, CW
    Grubbs, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21): : 7155 - 7158
  • [10] Total synthesis of octalactin A via ring-closing metathesis reaction
    Buszek, KR
    Sato, N
    Jeong, Y
    [J]. TETRAHEDRON LETTERS, 2002, 43 (02) : 181 - 184
12345