Enantioselective Total Synthesis of Cerorubenic Acid-III via Type II [5+2] Cycloaddition Reaction

被引：2
|
作者：
Liu, Xin [1 ]
Liu, Junyang [1 ,2 ]
Wu, Jianlei [1 ]
Li, Chuang-Chuang [1 ]
机构：
[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Peoples R China
[2] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 16期
基金：
中国国家自然科学基金;
关键词：
ANICETUS-BENEFICUS ISHII; HOST SELECTION BEHAVIOR; RUBENS MASKELL HEMIPTERA; YASUMATSU HYMENOPTERA; NATURAL-PRODUCTS; RING-SYSTEMS; CONSTRUCTION; ENCYRTIDAE; STIMULANTS; CLEAVAGE;
D O I：
10.1021/acs.joc.1c00185
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first enantioselective total synthesis of cerorubenic acid-III is described in detail. Different strategies and attempts, based on a type II [5+2] cycloaddition reaction, leading to the bicyclo[4.4.1] ring system with a strained bridgehead double bond, are depicted. Furthermore, sodium naphthalenide was found to be efficient in the chemoselective reduction of 8-oxabicyclo[3.2.1]octene, with three transformations completed in one operation. An unusual S(N)1 transannular cyclization reaction was applied to construct the synthetically challenging vinylcyclopropane moiety. This strategy enabled the total synthesis of cerorubenic acid-III in 19 steps.
引用
收藏
页码：11125 / 11139
页数：15
相关论文
共 50 条
  • [11] Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5+2] Cycloaddition
    Zhang, Min
    Liu, Na
    Tang, Weiping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) : 12434 - 12438
  • [12] STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF CERORUBENIC ACID-III .2. ANALYSIS OF THE INABILITY TO REALIZE D-RING FORMATION BY MEANS OF EXTRAANNULAR ROBINSON ANNULATION
    PAQUETTE, LA
    LASSALLE, GY
    LOVELY, CJ
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16): : 4254 - 4261
  • [13] Formal total synthesis of (±)-hirsutic acid C using the tandem Rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction
    Yuan, Changxia
    Jiao, Lei
    Yu, Zhi-Xiang
    TETRAHEDRON LETTERS, 2010, 51 (43) : 5674 - 5676
  • [14] Expedient synthesis of a highly substituted tropolone via a 3-oxidopyrylium [5+2] cycloaddition reaction
    Baldwin, JE
    Mayweg, AVW
    Pritchard, GJ
    Adlington, RM
    TETRAHEDRON LETTERS, 2003, 44 (24) : 4543 - 4545
  • [15] Type II Intramolecular [5+2] Cycloaddition: Facile Synthesis of Highly Functionalized Bridged Ring Systems
    Mei, Guangjian
    Liu, Xin
    Qiao, Chuang
    Chen, Wei
    Li, Chuang-chuang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) : 1754 - 1758
  • [16] Synthesis of 1-acetyl-2-silyoxycycloheptane derivatives via highly stereoselective formal [5+2] cycloaddition reaction
    Kudo, Mami
    Kondo, Fumikatsu
    Maekawa, Hideki
    Shimizu, Tadashi
    Miyashita, Masaaki
    Tanino, Keiji
    TETRAHEDRON LETTERS, 2014, 55 (06) : 1192 - 1195
  • [17] Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5+2] Cycloaddition
    Qu, Chunlei
    Chen, Lu
    Wang, Peng
    Zhang, Jingwei
    Ding, Yiming
    Long, Xianwen
    Zhang, Tingrong
    Zhao, Yaqiu
    Deng, Jun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (08) : 6739 - 6746
  • [18] Total synthesis of (+)-frondosin A. Application of the RU-catalyzed [5+2] cycloaddition
    Trost, Barry M.
    Hu, Yimin
    Horne, Daniel B.
    Journal of the American Chemical Society, 2007, 129 (38): : 11781 - 11790
  • [19] Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+2] cycloaddition
    Trost, Barry M.
    Hu, Yimin
    Horne, Daniel B.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (38) : 11781 - 11790
  • [20] Studies toward the synthesis of arteminolide: [5+2] cycloaddition reaction of allenes with oxidopyrylium ions
    Lee, HY
    Sohn, JH
    Kim, HY
    TETRAHEDRON LETTERS, 2001, 42 (09) : 1695 - 1698
12345