Catalytic Asymmetric Total Synthesis of Tangutorine

被引:25
|
作者
Nemoto, Tetsuhiro [1 ]
Yamamoto, Eri [1 ]
Franzen, Robert [1 ]
Fukuyama, Takashi [1 ]
Wu, Riliga [1 ]
Fukamachi, Toshihiko [1 ]
Kobayashi, Hiroshi [1 ]
Hamada, Yasumasa [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
CHIROGENIC DIAMINOPHOSPHINE OXIDES; STEREOSELECTIVE TOTAL-SYNTHESIS; ALLYLIC SUBSTITUTION; PALLADIUM; DIAPHOXS; ACID; (+/-)-TANGUTORINE; NUCLEOPHILES; DERIVATIVES; CYCLIZATION;
D O I
10.1021/ol902929a
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 tangutorine has been achieved, wherein a Pd-catalyzed asymmetric allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand was the key step.
引用
收藏
页码:872 / 875
页数:4
相关论文
共 50 条
  • [41] Catalytic Asymmetric Total Synthesis of Macrocyclic Marine Natural Product (-)-Haliclonin A
    Luo, Shi-Peng
    Huang, Xiong-Zhi
    Guo, Lian-Dong
    Huang, Pei-Qiang
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1723 - 1736
  • [42] Efforts toward the total synthesis of apoptolidin C: A catalytic, asymmetric approach
    Hale, James S.
    Nelson, Scott G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [43] Catalytic asymmetric total synthesis of the muscarinic receptor antagonist (R)-tolterodine
    Hedberg, C
    Andersson, PG
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) : 662 - 666
  • [44] Catalytic Asymmetric Total Synthesis of (-)-Garryine via an Enantioselective Heck Reaction
    Li, Chuang
    Lu, Fei
    Cai, Yukun
    Zhang, Cheng
    Shao, Yu
    Zhang, Yuanyuan
    Liu, Xiao-Yu
    Qin, Yong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 146 (01) : 1081 - 1088
  • [45] Tangutorine: Synthesis, Biogenetic Relationship and Biomimetic Synthesis
    Tu, Xiaojun
    Liu, Jianli
    Wang, Cuiling
    Liu, Chen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (10) : 1584 - 1592
  • [46] Catalytic asymmetric synthesis
    Denmark, SE
    Jacobsen, EN
    ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 324 - 324
  • [48] Silver salt effects on an asymmetric Heck reaction. Catalytic asymmetric total synthesis of (+)-xestoquinone.
    Miyazaki, F
    Uotsu, K
    Shibasaki, M
    TETRAHEDRON, 1998, 54 (43) : 13073 - 13078
  • [49] Total synthesis of (+)-hygrine via asymmetric phase-transfer catalytic alkylation
    Lee, Jeong-Hee
    Jeong, Byeong-Seon
    Ku, Jin-Mo
    Jew, Sang-sup
    Park, Hyeung-geun
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17): : 6690 - 6692
  • [50] Asymmetric Total Synthesis of (-)-Amphidinolide V through Effective Combinations of Catalytic Transformations
    Volchkov, Ivan
    Lee, Daesung
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5324 - 5327