Bioinspired Total Synthesis of Agelastatin A

被引：58
作者：
Reyes, Jeremy Chris P. [1 ]
Romo, Daniel [1 ]
机构：
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 28期
关键词：
alkaloids; biomimetic synthesis; N-acyliminium; Nazarov cyclization; pyrrole-2-amino imidazole alkaloids; PYRROLE-IMIDAZOLE ALKALOIDS; MARINE NATURAL-PRODUCTS; CORAL SEA; SIGMATROPIC REARRANGEMENT; ABSOLUTE-CONFIGURATION; ALKYNYLIODONIUM SALTS; ORGANIC-SYNTHESIS; (-)-AGELASTATIN; DENDROMORPHA; ACID;
D O I：
10.1002/anie.201200959
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A one-two punch: Two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A (see scheme). A diastereoselective C-ring formation, which proceeds through a 5-exo-trig cyclization or a Nazarov cyclization of a red-colored N-acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：6870 / 6873
页数：4
相关论文
共 59 条
  • [1] Akiyama T., 2006, Patent U.S., Patent No. [0276329 A1, 0276329]
  • [2] Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
  • [3] Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids
    Al-Mourabit, Ali
    Zancanella, Manuel A.
    Tilvi, Supriya
    Romo, Daniel
    [J]. NATURAL PRODUCT REPORTS, 2011, 28 (07) : 1229 - 1260
  • [4] Studies on total synthesis of the cytotoxic marine alkaloid agelastatin A
    Anderson, GT
    Chase, CE
    Koh, YH
    Stien, D
    Weinreb, SM
    Shang, MY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7594 - 7595
  • [5] Nagelamide J, a novel dimeric bromopyrrole alkaloid from a sponge Agelas species
    Araki, Atsushi
    Tsuda, Masashi
    Kubota, Takaaki
    Mikami, Yuzuru
    Fromont, Jane
    Kobayashi, Jun'ichi
    [J]. ORGANIC LETTERS, 2007, 9 (12) : 2369 - 2371
  • [6] Synthesis and reactions of cyclopentadiene monoaziridine: a concise approach to the core of agelastatin A
    Baron, E
    O'Brien, P
    Towers, TD
    [J]. TETRAHEDRON LETTERS, 2002, 43 (04) : 723 - 726
  • [7] AGELASTATIN-A, A NEW SKELETON CYTOTOXIC ALKALOID OF THE OROIDIN FAMILY - ISOLATION FROM THE AXINELLID SPONGE AGELAS-DENDROMORPHA OF THE CORAL SEA
    DAMBROSIO, M
    GUERRIERO, A
    DEBITUS, C
    RIBES, O
    PUSSET, J
    LEROY, S
    PIETRA, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) : 1305 - 1306
  • [8] DAMBROSIO M, 1994, HELV CHIM ACTA, V77, P1895
  • [9] The active centres of agelastatin A, a strongly cytotoxic alkaloid of the Coral Sea axinellid sponge Agelas dendromorpha, as determined by comparative bioassays with semisynthetic derivatives
    DAmbrosio, M
    Guerriero, A
    Ripamonti, M
    Debitus, C
    Waikedre, J
    Pietra, F
    [J]. HELVETICA CHIMICA ACTA, 1996, 79 (03) : 727 - 735
  • [10] Asymmetric total synthesis of (-)-agelastatin A using sulfinimine (N-sulfinyl imine) derived methodologies
    Davis, FA
    Deng, J
    [J]. ORGANIC LETTERS, 2005, 7 (04) : 621 - 623
123456