Au-Catalyzed [2+3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H

被引：37
|
作者：
Ma, Xiao-Yan [1 ]
An, Man-Tao [1 ]
Zhao, Xian-He [1 ]
Du, Ji-Yuan [1 ,3 ]
Deng, Yu-Hua [1 ]
Zhang, Xiang-Zhi [1 ]
Fan, Chun-An [1 ,2 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
[3] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 11期
关键词：
VERSATILE BUILDING-BLOCKS; FORMAL SYNTHESIS; GOLD CATALYSIS; NATURAL-PRODUCTS; CYCLIZATION; DERIVATIVES; ALKALOIDS; ACCESS;
D O I：
10.1021/acs.orglett.7b01202
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel Au-catalyzed [2 + 3] annulation reaction of enamides with propargyl esters has been developed, providing a new method for expeditious assembly of synthetically useful functionalized 1-azaspiro[4.4]nonane building blocks. Based on this key annulation, strategic installation of the pivotal azaspirocyclic core, followed by constructing the benzazepine unit via Witkop cyclization, led to the divergent total syntheses of cephalotaxine and cephalezomine H.
引用
收藏
页码：2965 / 2968
页数：4
相关论文
共 50 条
  • [1] FORMAL TOTAL SYNTHESIS OF IPOMEAMARONE VIA THE [2+3] DIHYDROFURAN ANNULATION
    HUDLICKY, T
    LOVELACE, TC
    SYNTHETIC COMMUNICATIONS, 1990, 20 (11) : 1721 - 1732
  • [2] Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3+2] Cycloaddition of Enynyl Esters
    Zheng, Huaiji
    Huo, Xing
    Zhao, Changgui
    Jing, Peng
    Yang, Juan
    Fang, Bowen
    She, Xuegong
    ORGANIC LETTERS, 2011, 13 (24) : 6448 - 6451
  • [3] Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)-H Site
    Shiroodi, Roohollah Kazem
    Sugawara, Masumi
    Ratushnyy, Maxim
    Yarbrough, Douglas C.
    Wink, Donald J.
    Gevorgyan, Vladimir
    ORGANIC LETTERS, 2015, 17 (16) : 4062 - 4065
  • [4] A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles
    Xie, Haodong
    Zhao, Wei
    Wei, Heping
    Yu, Yang
    Zhao, Lili
    Baell, Jonathan B.
    Huang, Fei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4546 - 4555
  • [5] Asymmetric Synthesis of Pyrroloindolones by N-Heterocyclic Carbene Catalyzed [2+3] Annulation of α-Chloroaldehydes with Nitrovinylindoles
    Ni, Qijian
    Zhang, Huan
    Grossmann, Andre
    Loh, Charles C. J.
    Merkens, Carina
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) : 13562 - 13566
  • [6] STEREOCONTROLLED TOTAL SYNTHESIS OF PENTALENENES VIA [2+3] AND [4+1] CYCLOPENTENE ANNULATION METHODOLOGIES
    HUDLICKY, T
    NATCHUS, MG
    SINAIZINGDE, G
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20): : 4641 - 4644
  • [7] Application of the phosphine catalyzed (3+2) annulation: Total synthesis of ibophyllidine
    Andrews, Ian P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [8] N-heterocyclic carbene catalyzed [2+3] annulation reaction for the synthesis of trifluoroethyl 3,2′-spirooxindole γ-lactam
    Pu, Yiru
    Wang, Maolin
    Tian, Wanrong
    Ge, Xian
    Zhu, Dikai
    Wang, Chuanqi
    Zeng, Yingjie
    Tao, Feiyan
    Deng, Yun
    Lu, Jun
    RSC ADVANCES, 2024, 14 (26) : 18453 - 18458
  • [9] Au(I)-Catalyzed Annulation of Propargyl Amine with Aldehydes: One-Pot Cascade Synthesis of 2,5-Dimethylpyrazines
    Su, Ji
    Liu, Huixin
    Hua, Ruimao
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2015, 16 (02) : 3599 - 3608
  • [10] EosinY and copper-catalyzed oxidative [2+3] annulation of glycine esters with oxiranes and thiiranes under light free conditions
    Chowdhury, Raghunath
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025,
12345