Aza-annulation strategies in alkaloid total synthesis

被引:26
作者
Lawrence, Adrien K. [1 ]
Gademann, Karl [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Swiss Fed Inst Technol, Chem Synth Lab, SB ISIC LSYNC, CH-1015 Lausanne, Switzerland
来源
SYNTHESIS-STUTTGART | 2008年 / 03期
关键词
biomimetic synthesis; cyclizations; natural products; stereoselective synthesis; total synthesis;
D O I
10.1055/s-2008-1032134
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review highlights the synthesis of nitrogen-containing natural products via aza-annulation. Strategic, tactical, and methodological perspectives are discussed, including recent developments such as metal- or organocatalyzed reactions, oxidative or reductive cyclizations, biomimetic processes, cascade reactions, and cycloadditions. Such key steps are presented in the context of the total syntheses of tropinone, batzelladine, lyconadin, FR901483, strychnofoline, discorhabdin, necatarone, aspidophytine, dibromophakellstatin, anachelin, the acridones, alkaloid GB 13, cephalotaxine, strychnine, setoclavine, porantherine, vallesamine, nitraramine, cylindricine, the daphniphyllines, symbiomime, alstonerine, tangutorine and flustramine.
引用
收藏
页码:331 / 351
页数:21
相关论文
共 322 条
  • [1] Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine C, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization
    Abe, H
    Aoyagi, S
    Kibayashi, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) : 1473 - 1480
  • [2] BIOMIMETIC SYNTHESIS OF ACRIDONE ALKALOIDS
    ADAMS, JH
    GUPTA, P
    KHAN, MS
    LEWIS, JR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (19): : 2173 - 2177
  • [3] The epindoline group Part I Trial of various methods for the synthesis of epindolidiones
    Ainley, AD
    Robinson, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1934, : 1508 - 1520
  • [4] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
  • [5] 2-5
  • [6] ANGENOT L, 1978, Plantes Medicinales et Phytotherapie, V12, P123
  • [7] [Anonymous], 1955, STRUCTURAL RELATIONS
  • [8] Total synthesis of (+)-cylindricine C
    Arai, T
    Abe, H
    Aoyagi, S
    Kibayashi, C
    [J]. TETRAHEDRON LETTERS, 2004, 45 (30) : 5921 - 5924
  • [9] SULFURANES .6. REACTIONS INVOLVING ALKOXY LIGANDS OF DIALKOXYDIARYLSULFURANES - FORMATION OF OLEFINS AND ETHERS
    ARHART, RJ
    MARTIN, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) : 5003 - &
  • [10] Diastereoselective [4+2] annulation of vinyl carbodiimides with N-alkyl imines.: Asymmetric synthetic access to the batzelladine alkaloids
    Arnold, MA
    Durón, SG
    Gin, DY
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) : 6924 - 6925