A highly stereocontrolled total synthesis of (-)-neodysiherbaine A

被引:29
|
作者
Takahashi, Keisuke [1 ]
Matsumura, Takashi [1 ]
Corbin, Graeme R. M. [1 ]
Ishihara, Jun [1 ]
Hatakeyama, Susumi [1 ]
机构
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 11期
关键词
D O I
10.1021/jo060410r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Neodysiherbaine A, a neuroexitotoxin occurring in a Micronesian marine sponge Dysidea herbacea, was synthesized from tri-O-acetyl-D-glucal with excellent stereocontrol. The method established enables us to obtain gram quantities of neodysiherbaine A and its related compounds.
引用
收藏
页码:4227 / 4231
页数:5
相关论文
共 50 条
  • [1] Total synthesis of dysiherbaine and neodysiherbaine A
    Cachet, Xavier
    Poree, Francois-Hugues
    RSC ADVANCES, 2013, 3 (31): : 12466 - 12484
  • [2] A highly stereocontrolled total synthesis of dysiherbaine
    Takahashi, Keisuke
    Matsumura, Takashi
    Ishihara, Jun
    Hatakeyama, Susumi
    CHEMICAL COMMUNICATIONS, 2007, (40) : 4158 - 4160
  • [3] A Formal Total Synthesis of Dysiherbaine and Neodysiherbaine A
    Lee, Hee-Yoon
    Lee, Sang-Shin
    Kim, Hoon Seok
    Lee, Kang Mun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4192 - 4199
  • [4] Highly efficient stereocontrolled total synthesis of (+)-upial
    Takahashi, Kazunori
    Watanabe, Masayuki
    Honda, Toshio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 131 - 133
  • [5] Highly stereocontrolled total synthesis of (+)-bengamide E
    J Chem Soc Perkin Trans 1, (2849):
  • [6] HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-ALLOPUMILIOTOXIN-339A
    AOYAGI, S
    WANG, TC
    KIBAYASHI, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10653 - 10654
  • [7] A SIMPLE, HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-HIRSUTIC ACID
    SHIBASAKI, M
    YAMAZAKI, M
    ISEKI, K
    IKEGAMI, S
    TETRAHEDRON LETTERS, 1982, 23 (50) : 5311 - 5314
  • [8] HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-BENGAMIDE-E
    MUKAI, C
    MOHARRAM, SM
    KATAOKA, O
    HANAOKA, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (22): : 2849 - 2854
  • [9] Highly stereocontrolled total synthesis of secodolastane diterpenoid isolinearol
    Kobayashi, Toyoharu
    Tomita, Yui
    Kawamoto, Yuichiro
    Ito, Hisanaka
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (37) : 7316 - 7320
  • [10] Total synthesis and biological evaluation of neodysiherbaine A and analogues
    Shoji, Muneo
    Akiyama, Nobuyuki
    Tsubone, Koichi
    Lash, L. Leanne
    Sanders, James M.
    Swanson, Geoffrey T.
    Sakai, Ryuichi
    Shimamoto, Keiko
    Oikawa, Masato
    Sasaki, Makoto
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14): : 5208 - 5220