Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

被引：7
|
作者：
Sacher, Joshua R. [1 ]
Weinreb, Steven M. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
TETRAHEDRON | 2011年 / 67卷 / 52期
基金：
美国国家科学基金会;
关键词：
Natural product; Alkaloid; Diels-Alder; Henry reaction; Catalytic hydrogenation; MASKED O-BENZOQUINONES; DIELS-ALDER REACTIONS; ANTICAPSIN;
D O I：
10.1016/j.tet.2011.04.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A strategy for a total synthesis of the structurally novel Lyco podium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective Diels-Alder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10203 / 10207
页数：5
相关论文
共 50 条
  • [1] Progress towards the Total Syntheses of Lycopodium Alkaloid, Lycopladine A
    Rodrigues, Lima
    Majik, Mahesh Satu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1151 - 1163
  • [2] Asymmetric total synthesis of Lycopodium alkaloid (+)-lycopladine A
    Xu, Tao
    Luo, Xiu-Li
    Yang, Yu-Rong
    TETRAHEDRON LETTERS, 2013, 54 (22) : 2858 - 2860
  • [3] Lycopladine H, a novel alkaloid with fused-tetracyclic skeleton from Lycopodium complanatum
    Ishiuchi, Kan'ichiro
    Kubota, Takaaki
    Hayashi, Shigeki
    Shibata, Toshiro
    Kobayashi, Jun'chi
    TETRAHEDRON LETTERS, 2009, 50 (47) : 6534 - 6536
  • [4] Synthesis of the Tetracyclic Skeleton of the Lycopodium Alkaloid Lycopladine H via a Pivotal Double Hydroformylation/Intramolecular Reductive Amination Sequence
    Chauhan, Pradeep S.
    Sacher, Joshua R.
    Weinreb, Steven M.
    ORGANIC LETTERS, 2015, 17 (04) : 806 - 808
  • [5] Progress towards the total synthesis of the Lycopodium alkaloid (+)-fastigiatine
    Samame, Renzo A.
    Rychnovsky, Scott D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [6] Synthetic studies towards novel tetracyclic Lycopodium alkaloids: A synthesis of deoxymagellaninone
    Mehta, G
    Reddy, MS
    Thomas, A
    TETRAHEDRON, 1998, 54 (27) : 7865 - 7882
  • [7] Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine
    Comins, DL
    Williams, AL
    ORGANIC LETTERS, 2001, 3 (20) : 3217 - 3220
  • [8] Total synthesis of the Lycopodium alkaloid (+)-sieboldine A
    Canham, Stephen M.
    France, David J.
    Overman, Larry E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [9] Total Synthesis of the Lycopodium Alkaloid (+)-Serratezomine A
    Chandra, Aroop
    Pigza, Julie A.
    Han, Jeong-Seok
    Mutnick, Daniel
    Johnston, Jeffrey N.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) : 3470 - +
  • [10] Construction of the Azocane (Azacyclooctane) Moiety of the Lycopodium Alkaloid Lycopladine H via an Intramolecular Hydroaminomethylation Strategy
    Sacher, Joshua R.
    Weinreb, Steven M.
    ORGANIC LETTERS, 2012, 14 (08) : 2172 - 2175
12345