Benzosceptrins A and B with a Unique Benzocyclobutane Skeleton and Nagelamide S and T from Pacific Sponges

被引：45
作者：
Appenzeller, Jerome [1 ]
Tilvi, Supriya [1 ]
Martin, Marie-Therese [1 ]
Gallard, Jean-Francois [1 ]
El-bitar, Hoda [1 ]
Dau, Elise Tran Huu [1 ]
Debitus, Cecile [2 ]
Laurent, Dominique [3 ]
Moriou, Celine [1 ]
Al-Mourabit, Ali [1 ]
机构：
[1] CNRS, UPR 2301, Inst Chim Subst Nat, Ctr Rech Gif Sur Yvette, Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Ctr Polynesien Rech Biodiversite Insulaire, IRD UMR 152, Papeete, France
[3] Univ Toulouse 3, UMR IRD 152, F-31062 Toulouse 9, France
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 21期
关键词：
DIMERIC BROMOPYRROLE ALKALOIDS; AGELAS; 2-AMINOIMIDAZOLE; PROLINE; OROIDIN;
D O I：
10.1021/ol901946h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Four new dimeric pyrrole-2-aminoimidazole alkaloids have been isolated from the Pacific marine sponges Agelas cf. mauritiana and Phakellia sp. They include the unusual C2 symmetrical benzosceptrins A (4) and B (5), which each possess a unique benzocyclobutane skeleton and nagelamides S (6) and T (7). Their structures and relative configuration were elucidated from spectroscopic data. Plausible biogenetic paths for these compounds are also proposed in this paper.
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收藏
页码：4874 / 4877
页数：4
相关论文
共 22 条
  • [1] Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids:: Ab initio calculations, tautomerism, and reactivity
    Abou-Jneid, R
    Ghoulami, S
    Martin, MT
    Dau, ETH
    Travert, N
    Al-Mourabit, A
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 3933 - 3936
  • [2] Aiello A., 2008, Modern alkaloids structure, isolation, synthesis and biology by, P271, DOI [10.1002/9783527621071.ch10, DOI 10.1002/9783527621071.CH10]
  • [3] Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
  • [4] Agelasines J, K, and L from the Solomon Islands marine sponge Agelas cf. mauritiana
    Appenzeller, Jerome
    Mihci, Ghezala
    Martin, Marie-Therese
    Gallard, Jean-Francois
    Menou, Jean-Louis
    Boury-Esnalllt, Nicole
    Hooper, John
    Petek, Sylvain
    Chevalley, Severine
    Valentin, Alexis
    Zaparucha, Anne
    Al-Mourabit, Ali
    Debitus, Cecile
    [J]. JOURNAL OF NATURAL PRODUCTS, 2008, 71 (08): : 1451 - 1454
  • [5] Nagelamides K and L, dimeric bromopyrrole alkaloids from sponge Agelas species
    Araki, Atsushi
    Kubota, Takaaki
    Tsuda, Masashi
    Mikami, Yuzuru
    Fromont, Jane
    Kobayashi, Jun'ichi
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2099 - 2102
  • [6] 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
  • [7] Nagelamides Q and R, Novel Dimeric Bromopyrrole Alkaloids from Sponges Agelas sp.
    Araki, Atsushi
    Kubota, Takaaki
    Aoyama, Kazuki
    Mikami, Yuzuru
    Fromont, Jane
    Kobayashi, Jun'ichi
    [J]. ORGANIC LETTERS, 2009, 11 (08) : 1785 - 1788
  • [8] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
    DEWAR, MJS
    ZOEBISCH, EG
    HEALY, EF
    STEWART, JJP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
  • [9] Nagelamides A-H, new dimeric bromopyrrole alkaloids from marine sponge Agelas species
    Endo, T
    Tsuda, M
    Okada, T
    Mitsuhashi, S
    Shima, H
    Kikuchi, K
    Mikami, Y
    Fromont, J
    Kobayashi, J
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08): : 1262 - 1267
  • [10] NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES
    FORENZA, S
    MINALE, L
    RICCIO, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18): : 1129 - &
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