Synthesis of the tricyclic core structure of vindoline

被引:24
|
作者
Guo, ZH [1 ]
Schultz, AG [1 ]
机构
[1] Rensselaer Polytech Inst, Dept Chem, Troy, NY 12180 USA
关键词
vindoline; synthesis; 1,3-dipolar cycloaddition; birch reduction-alkylation;
D O I
10.1016/j.tetlet.2003.11.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of the core tricyclic structure (18) of vindoline has been achieved using the strategy, which features an intramolecular 1,3-dipolar cycloaddition of the azido dienone (12) to give aziridine (13) with complete region- and stereocontrol. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:919 / 921
页数:3
相关论文
共 50 条
  • [21] Synthesis of the tricyclic core of the marine alkaloid Lepadiformine
    Hunter, R
    Richards, P
    SYNLETT, 2003, (02) : 271 - 273
  • [22] Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules
    Sunden, Henrik
    Olsson, Roger
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (21) : 4831 - 4833
  • [23] Concise synthesis of the tricyclic core of lycoposerramine S
    Elliott, Mark C.
    El Sayed, Nahed N. E.
    Paine, James S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) : 2611 - 2618
  • [24] Synthesis of the BCD Tricyclic Core of Densanins A and B
    Shi, Shan
    Shi, HongWei
    Li, JianLong
    Li, Fei
    Chen, Lei
    Zhang, Chao
    Huang, ZhiYan
    Zhao, Na
    Li, Nan
    Yang, Jun
    ORGANIC LETTERS, 2016, 18 (09) : 1949 - 1951
  • [25] TOTAL SYNTHESIS OF (+/-)-VINDOLINE
    ANDO, M
    BUCHI, G
    OHNUMA, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) : 6880 - 6881
  • [26] Synthesis of the tricyclic core of eleutherobin and sarcodictyins and total synthesis of sarcodictyin A
    Nicolaou, KC
    Xu, JY
    Kim, S
    Ohshima, T
    Hosokawa, S
    Pfefferkorn, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) : 11353 - 11354
  • [27] Total synthesis of (-)-vindoline
    Chen, Wen
    Tian, Hongchang
    Tan, Wenyun
    Liu, Xiaotong
    Yang, Xiaodong
    Zhang, Hongbin
    TETRAHEDRON, 2019, 75 (12) : 1751 - 1759
  • [28] Synthesis of the tricyclic triamine core of martinelline and martinellic acid
    Snider, BB
    Ahn, Y
    Foxman, BM
    TETRAHEDRON LETTERS, 1999, 40 (17) : 3339 - 3342
  • [29] Synthesis of the tricyclic core of the marine natural product labiatin A
    Clark, JS
    Baxter, CA
    Castro, JL
    SYNTHESIS-STUTTGART, 2005, (19): : 3398 - 3404
  • [30] Synthesis of the tricyclic core of the complex marine alkaloid (±)-halichlorine
    Perkins, AL
    Feldman, KS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U170 - U170