Synthetic studies on breviones: construction of the CDE ring system

被引：16
|
作者：
Takikawa, H
Hirooka, M
Sasaki, M
机构：
[1] Kobe Univ, Dept Biofunct Chem, Nada Ku, Kobe, Hyogo 6578501, Japan
[2] Kobe Univ, Ctr Cooperat Res & Dev, Nada Ku, Kobe, Hyogo 6578501, Japan
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 09期
关键词：
diterpenoids; allelopathic agents; tandem reaction; palladium catalyst;
D O I：
10.1016/S0040-4039(02)00081-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Breviones A-E (1-5), allelopathic agents isolated from Penicillium brevicompactum Dierckx, are structurally unique pentacyclic or hexacyclic diterpenoid derivatives. The synthesis of a structurally simplified model compound (8), corresponding to the characteristic spiro-fused CDE ring portion of 1-4, was accomplished by employing sequential, double nucleophilic substitution reactions as the key steps. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码：1713 / 1716
页数：4
相关论文
共 50 条
  • [31] Synthetic study of andrastins: stereoselective construction of the BCD-ring system
    Fumihiko Yoshimura
    Taiki Abe
    Yuichi Ishioka
    Keiji Tanino
    The Journal of Antibiotics, 2019, 72 : 384 - 388
  • [32] NEW SYNTHETIC STRATEGY FOR THE CONSTRUCTION OF THE BCD RING-SYSTEM OF TANSHINONES
    SHISHIDO, K
    TAKATA, T
    OMODANI, T
    SHIBUYA, M
    CHEMISTRY LETTERS, 1993, (03) : 557 - 560
  • [33] Synthetic studies towards pentacyclic quassinoids: Facile and stereocontrolled construction of the E ring
    Shing, TKM
    Zhu, XY
    Mak, TCW
    TETRAHEDRON-ASYMMETRY, 1996, 7 (03) : 673 - 676
  • [34] SYNTHETIC STUDIES ON DENSANINS: STEREOSELECTIVE CONSTRUCTION OF A PYRROLIDINE RING CONTAINING A QUATERNARY CARBON
    Ueda, Kyosuke
    Yokoshima, Satoshi
    HETEROCYCLES, 2021, 103 (01) : 172 - 176
  • [35] Synthetic studies toward the kempane diterpenes: Preparation of the ring system
    Liu, CJ
    Burnell, DJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) : 9584 - 9585
  • [36] Synthetic studies on asperparaline A. Synthesis of the spirosuccinimide ring system
    Gonzalez, F
    Sanz-Cervera, JF
    Williams, RM
    TETRAHEDRON LETTERS, 1999, 40 (24) : 4519 - 4522
  • [37] Synthetic studies toward the kempane diterpenes: Preparation of the ring system
    J Am Chem Soc, 40 (9584):
  • [38] Synthetic Studies Towards the Core Tricyclic Ring System of Pradimicin A
    Zilke, Laura
    Hall, Dennis G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4153 - 4163
  • [39] SYNTHETIC STUDIES TOWARD CONCAVINE: SYNTHESIS OF THE BCD RING SYSTEM
    Komori, Yosuke
    Kozen, Akitoshi
    Toyota, Masahiro
    HETEROCYCLES, 2016, 93 (02) : 792 - 801
  • [40] Using singlet oxygen to synthesise the CDE-ring system of the pectenotoxins
    Kouridaki, Antonia
    Montagnon, Tamsyn
    Kalaitzakis, Dimitris
    Vassilikogiannakis, Georgios
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) : 537 - 541
12345