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
  • [21] Catalytic Asymmetric Hydrogenation of α-Arylcyclohexanones and Total Synthesis of (-)-α-Lycorane
    Li, Gang
    Xie, Jian-Hua
    Hou, Jing
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) : 1597 - 1604
  • [22] Catalytic Asymmetric Total Synthesis of ent-Hyperforin
    Shimizu, Yohei
    Shi, Shi-Liang
    Usuda, Hiroyuki
    Kanai, Motomu
    Shibasaki, Masakatsu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (06) : 1103 - 1106
  • [23] Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C
    Sun, Wang-Bin
    Wang, Xuan
    Sun, Bing-Feng
    Zou, Jian-Ping
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2016, 18 (06) : 1219 - 1221
  • [24] Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene
    Chandler, Carley L.
    List, Benjamin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) : 6737 - +
  • [25] Synthesis of the tangutorine skeleton
    Berner, M
    Tolvanen, A
    Jokela, R
    TETRAHEDRON LETTERS, 1999, 40 (39) : 7119 - 7122
  • [26] Asymmetric Total Synthesis of Alstrostine G Utilizing a Catalytic Asymmetric Desymmetrization Strategy
    Zhang, Nanping
    Wang, Cheng
    Xu, Hailong
    Zheng, Ming
    Jiang, Huanfeng
    Chen, Kai
    Ma, Zhiqiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (34)
  • [27] Towards the total synthesis of tangutorine by intramolecular Diels-Alder reaction
    Wilkinson, JA
    Ardes-Guisot, N
    Ducki, S
    Leonard, J
    TETRAHEDRON LETTERS, 2005, 46 (46) : 8053 - 8056
  • [28] The first catalytic asymmetric total synthesis of ent-hyperforin
    Shimizu, Yohei
    Shi, Shi-Liang
    Usuda, Hiroyuki
    Kanai, Motomu
    Shibasaki, Masakatsu
    TETRAHEDRON, 2010, 66 (33) : 6569 - 6584
  • [29] Catalytic asymmetric preparation of pyrroloindolines: strategies and applications to total synthesis
    Mei, Guang-Jian
    Koay, Wai Lean
    Tan, Chuan Xiang Alvin
    Lu, Yixin
    CHEMICAL SOCIETY REVIEWS, 2021, 50 (10) : 5985 - 6012
  • [30] Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione
    O'Hora, Paul S.
    Incerti-Pradillos, Celia A.
    Kabeshov, Mikhail A.
    Shipilovskikh, Sergei A.
    Rubtsov, Aleksandr E.
    Elsegood, Mark R. J.
    Malkov, Andrei V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (12) : 4551 - 4555