Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles Rearrangement Reaction

被引:18
|
作者
Lan, Ping [1 ]
Jackson, Colin J. [1 ]
Banwell, Martin G. [1 ]
Willis, Anthony C. [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
来源
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 14期
基金
澳大利亚研究理事会;
关键词
INTRAMOLECULAR HECK REACTION; ALZHEIMERS-DISEASE; ACETYLCHOLINESTERASE INHIBITORS; AMARYLLIDACEAE ALKALOIDS; LEUCOJUM-AESTIVUM; SCALE PROCESS; (-)-GALANTHAMINE; (+/-)-GALANTHAMINE; GALANTAMINE; DERIVATIVES;
D O I
10.1021/jo501255c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.
引用
收藏
页码:6759 / 6764
页数:6
相关论文
共 50 条
  • [21] Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps
    Kotha, Sambasivarao
    Gunta, Rama
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1373 - 1378
  • [22] Design and synthesis of fused polycycles via Diels-Alder reaction and ring-rearrangement metathesis as key steps
    Kotha, Sambasivarao
    Ravikumar, Ongolu
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1259 - 1264
  • [23] Design and synthesis of oxa-bowls via Diels-Alder reaction and ring-rearrangement metathesis as key steps
    Kotha, Sambasivarao
    Ravikumar, Ongolu
    TETRAHEDRON LETTERS, 2014, 55 (42) : 5781 - 5784
  • [24] Synthesis of indoline-piperidinones via a novel Ugi, ring expansion, pseudo-Dieckmann condensation and rearrangement cascade reaction
    Lei, Jie
    Song, Gui-Ting
    Luo, Ya-Fei
    Tang, Dian-Yong
    Yan, Wei
    Li, Hong-yu
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (05) : 737 - 741
  • [25] Synthesis of Selenium-Containing N-Quinazolinyl Acroleins via a 3,3-Radical Rearrangement Cascade Reaction
    Wu, Qiong
    Zhang, Xinqin
    Yang, Qin
    Song, Zhibin
    Ding, Qiuping
    Peng, Yiyuan
    ORGANIC LETTERS, 2024, 26 (02) : 530 - 535
  • [26] Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition-Reduction-Cyclization Cascade
    Pang, Jian-Yu
    Feng, Li-Min
    Zhang, Wen-Feng
    Liu, De-Yong
    Wang, Jing
    Wei, Ruo-Han
    Hu, Xiang-Guo
    ORGANIC LETTERS, 2024, 27 (01) : 504 - 509
  • [27] TOTAL SYNTHESIS OF ACTINOMYCIN D(C1) VIA A RING-OPENING REACTION OF AZIRIDINE
    OKAWA, K
    NAKAJIMA, K
    TANAKA, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (08) : 1815 - 1816
  • [28] Synthetic studies towards the nor-triterpene pfaffic acid:: synthesis of DEF ring fragment via tandem radical cyclization rearrangement reactions
    Biju, PJ
    Kaliappan, K
    Rao, GSRS
    ARKIVOC, 2004, : 37 - 45
  • [29] Studies toward the total synthesis of di- and sesterterpenes with a dicyclopenta[a,d]cyclooctane skeleton.: Construction of a versatile A/B ring building block via a ring-closing metathesis reaction and carbocationic rearrangement
    Michalak, K
    Michalak, M
    Wicha, J
    TETRAHEDRON LETTERS, 2005, 46 (07) : 1149 - 1153
  • [30] Synthesis of Dibenz[b,f]oxepins via Manganese(III)-Based Oxidative 1,2-Radical Rearrangement
    Cong, Zhiqi
    Miki, Takumi
    Urakawa, Osamu
    Nishino, Hiroshi
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3978 - 3981