Total synthesis of (±)-Lingzhilactone B via semipinacol rearrangement

被引：14
|
作者：
Chen, Dong [1 ,2 ]
Li, Xiao-Mei [1 ,2 ]
Liu, Hao-Miao [1 ,2 ]
Li, Ming-Ming [3 ]
Cheng, Yong-Xian [1 ]
Qin, Hong-Bo [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Photochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Yunnan Baiyao Grp Corp Ltd, Kunming 650032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期
基金：
中国国家自然科学基金; 中国科学院西部之光基金;
关键词：
Total synthesis; Lingzhilactone B; Semipinacol rearrangement;
D O I：
10.1016/j.tetlet.2016.05.063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total synthesis of (+/-)-Lingzhilactone B has been achieved for the first time in 13 steps. The key step features a semipinacol rearrangement to construct 5/5 bicyclic ring with adjacent quaternary carbon. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2877 / 2879
页数：3
相关论文
共 50 条
  • [21] Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of (±)-Muscone
    Liu, Yi
    Yeung, Ying-Yeung
    ORGANIC LETTERS, 2017, 19 (06) : 1422 - 1425
  • [22] Enantioselective total synthesis of (-)-flustramines A, B and (-)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence
    Kawasaki, T
    Shinada, M
    Kamimura, D
    Ohzono, M
    Ogawa, A
    CHEMICAL COMMUNICATIONS, 2006, (04) : 420 - 422
  • [23] INDOLE ALKALOID SYNTHESIS VIA CLAISEN REARRANGEMENT - TOTAL SYNTHESIS OF SECODINE
    STRAUCHER
    MACDONALD, JE
    LAWRENCE, RF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) : 2419 - 2421
  • [24] Bronsted Acid Catalyzed Enantioselective Semipinacol Rearrangement for the Synthesis of Chiral Spiroethers
    Zhang, Qing-Wei
    Fan, Chun-An
    Zhang, Hai-Jun
    Tu, Yong-Qiang
    Zhao, Yu-Ming
    Gu, Peiming
    Chen, Zhi-Min
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (45) : 8572 - 8574
  • [25] A trifluoromethyl group directed semipinacol rearrangement: synthesis of a-(trifluoroacetyl) diarylmethanes
    J Fluorine Chem, 1 (49):
  • [26] Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover
    Taiga Kodo
    Kazunori Nagao
    Hirohisa Ohmiya
    Nature Communications, 13
  • [27] A boryl-migratory semipinacol rearrangement
    Dong-Hang Tan
    Zhi-Hao Chen
    Ling Yang
    Chang-Ting Li
    Fang-Hai Tu
    Qingjiang Li
    Honggen Wang
    Science China(Chemistry), 2022, 65 (04) : 746 - 752
  • [28] Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover
    Kodo, Taiga
    Nagao, Kazunori
    Ohmiya, Hirohisa
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [29] Semipinacol Rearrangement Induced by Cleavage of Dibromocyclopropane
    Kurimoto, Michitaka
    Nakajima, Daisuke
    Nishiyama, Yoshitake
    Yokoshima, Satoshi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4108 - 4111
  • [30] A boryl-migratory semipinacol rearrangement
    DongHang Tan
    ZhiHao Chen
    Ling Yang
    ChangTing Li
    FangHai Tu
    Qingjiang Li
    Honggen Wang
    Science China(Chemistry), 2022, (04) : 746 - 752
12345