The first enantioselective total synthesis of (-)-arisugacin A

被引：23
|
作者：
Cole, KP [1 ]
Hsung, RP [1 ]
机构：
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 48期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/S0040-4039(02)02094-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first enantioselective synthesis of (-)-arisugacin A in 17 steps is described here, featuring a CBS asymmetric ketone reduction and a highly stereoselective formal [3+3] cycloaddition approach. This concise synthesis of the enantiomer unambiguously confirms the original assignment of the absolute configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8791 / 8793
页数：3
相关论文
共 50 条
  • [1] The total synthesis of (±)-arisugacin A
    Cole, KP
    Hsung, RP
    Yang, XF
    TETRAHEDRON LETTERS, 2002, 43 (18) : 3341 - 3345
  • [2] The total synthesis of (±)-arisugacin A
    Hsung, RP
    Cole, KP
    Zehnder, LR
    Wang, JS
    Wei, LL
    Yang, XF
    Coverdale, HA
    TETRAHEDRON, 2003, 59 (03) : 311 - 324
  • [3] Total synthesis of arisugacin A.
    Cole, KP
    Hsung, RP
    Wang, JS
    Wei, LL
    Yang, XF
    Zehnder, LR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U216 - U217
  • [4] The first total synthesis of (±)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase
    Sunazuka, T
    Handa, M
    Nagai, K
    Shirahata, T
    Harigaya, Y
    Otoguro, K
    Kuwajima, I
    Omura, S
    ORGANIC LETTERS, 2002, 4 (03) : 367 - 369
  • [5] First enantioselective total synthesis of (-)-centrolobine
    Colobert, F
    Des Mazery, R
    Solladié, G
    Carreño, MC
    ORGANIC LETTERS, 2002, 4 (10) : 1723 - 1725
  • [6] First enantioselective total synthesis of altersolanol A
    Mechsner, Bastian
    Henssen, Birgit
    Pietruszka, Joerg
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (41) : 7674 - 7681
  • [7] First enantioselective total synthesis of (-)-tejedine
    Wang, YC
    Georghiou, PE
    ORGANIC LETTERS, 2002, 4 (16) : 2675 - 2678
  • [8] Synthetic efforts toward a total synthesis of (±) arisugacin A.
    Cole, KP
    Zehnder, LR
    Wei, LL
    Wang, JS
    Hsung, RP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U70 - U70
  • [9] First enantioselective total synthesis of (S)-(-)-longianone
    Perali, Ramu Sridhar
    Kalapati, Seshadri
    TETRAHEDRON, 2012, 68 (19) : 3725 - 3728
  • [10] First enantioselective total synthesis of (-)-heliannuol C
    Kamei, T
    Shindo, M
    Shishido, K
    TETRAHEDRON LETTERS, 2003, 44 (46) : 8505 - 8507
12345