Development and application of a convergent strategy for the total synthesis of polycyclic ether natural products

被引：0
|
作者：
Sasaki, Makoto [1 ]
机构：
[1] Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan
来源：
Bulletin of the Chemical Society of Japan | 2007年 / 80卷 / 05期
关键词：
The polycyclic ether class of marine natural products presents formidable and challenging synthetic targets due to their structural complexity and exceptionally potent biological activities. Over the past decade; however; their extremely limited availability from natural sources has precluded detailed biological studies on polycyclic ethers. Therefore; the supply of useful quantities of these natural products by chemical total synthesis has been strongly demanded. We developed a highly convergent strategy for the rapid assembly of a huge polycyclic ether array; which features Suzuki-Miyaura cross-coupling reaction of alkylboranes; generated from exocyclic enol ethers; with cyclic ketene acetal triffates or phosphates combined with reductive ring-closure. The utility of this strategy was demonstrated by its application to the convergent total synthesis of the natural products gambierol and gymnocin-A. These practical synthetic routes allowed for the first time systematic studies of the structure-activity relationships of the polycyclic ether class of natural products. © 2007 The Chemical Society of Japan;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Journal article (JA)
引用
收藏
页码：856 / 871
相关论文
共 50 条
  • [31] Total synthesis of natural products and development of synthetic methodologies
    Fukuyama, T
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U140 - U140
  • [32] TOTAL SYNTHESIS OF NATURAL PRODUCTS AND DEVELOPMENT OF NEW REAGENTS
    ACHIWA, K
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1971, 29 (05) : 461 - +
  • [33] Synthesis of Natural Products with Polycyclic Systems
    Yokoshima, Satoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (03) : 251 - 257
  • [34] Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products
    Lee, Hee-Yoon
    Song, Seog-Beom
    Kang, Taek
    Kim, Yoon Jung
    Geum, Su Jeong
    PURE AND APPLIED CHEMISTRY, 2013, 85 (04) : 741 - 753
  • [35] A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions
    Sakai, Takeo
    Sugimoto, Ai
    Mori, Yuji
    ORGANIC LETTERS, 2011, 13 (21) : 5850 - 5853
  • [36] Birch reduction and its application in the total synthesis of natural products
    Rao, GSRS
    PURE AND APPLIED CHEMISTRY, 2003, 75 (10) : 1443 - 1451
  • [37] Application of tert-Butanesulfinamide in Total Synthesis of Natural Products
    Li, Ying
    Ma, Zhiqiang
    Xu, Xuetao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (12) : 3991 - 4014
  • [38] Total synthesis of selected bioactive natural products: Illustration of strategy and design
    Tatsuta, K
    Hosokawa, S
    CHEMICAL REVIEWS, 2005, 105 (12) : 4707 - 4729
  • [39] Development of a strategy towards the total synthesis of aranotin and other dihydrooxepine-containing ETP natural products
    Codelli, Julian A.
    Puchlopek, Angela L.
    Reisman, Sarah E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [40] Total Synthesis of Polycyclic Natural Products via Photoenolization/Diels-Alder Reaction
    Yang, Baochao
    Hou, Min
    Gao, Shuanhu
    ACCOUNTS OF CHEMICAL RESEARCH, 2025,
12345