Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821

被引：14
作者：
Chen, Si-Kai [1 ,2 ]
Yang, Ju-Song [1 ,2 ]
Dai, Kun-Long [1 ,2 ]
Zhang, Fu-Min [1 ,2 ]
Zhang, Xiao-Ming [1 ,2 ]
Tu, Yong-Qiang [1 ,2 ,3 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China
[3] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 01期
关键词：
CONCISE TOTAL-SYNTHESIS; M-CHLOROPERBENZOIC ACID; C-H; IODINE; DIMERIZATION; ALKALOIDS; INDOLES; KETONES; (+)-CHIMONANTHINE; DEAROMATIZATION;
D O I：
10.1039/c9cc08646c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile and environmentally benign KI(cat.)/NaBO3 center dot 4H(2)O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a '-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I+" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.
引用
收藏
页码：121 / 124
页数：4
相关论文
共 56 条
  • [1] WIN 64821, A NEW COMPETITIVE ANTAGONIST TO SUBSTANCE-P, ISOLATED FROM AN ASPERGILLUS SPECIES - STRUCTURE DETERMINATION AND SOLUTION CONFORMATION
    BARROW, CJ
    CAI, P
    SNYDER, JK
    SEDLOCK, DM
    SUN, HH
    COOPER, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6016 - 6021
  • [2] Berthiol F., 2015, SYNTHESIS-STUTTGART, P587, DOI [DOI 10.1055/S-0034-1379892, 10.1055/s-0034-1379892]
  • [3] Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of N-Linked 2-(Azol-1-yl)indole Derivatives
    Beukeaw, Danupat
    Udomsasporn, Kwanchanok
    Yotphan, Sirilata
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) : 3447 - 3454
  • [4] I2/TBHP-Catalyzed Chemoselective Amination of Indoles
    Cai, Zhong-Jian
    Wang, Shun-Yi
    Ji, Shun-Jun
    [J]. ORGANIC LETTERS, 2013, 15 (20) : 5226 - 5229
  • [5] Combination of Tetrabutylammonium Iodide (TBAI) with tert-Butyl Hydroperoxide (TBHP): An Efficient Transition-Metal-Free System to Construct Various Chemical Bonds
    Chen, Rongxiang
    Chen, Jijun
    Zhang, Jie
    Wan, Xiaobing
    [J]. CHEMICAL RECORD, 2018, 18 (09) : 1292 - 1305
  • [6] Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine
    Chen, Si-Kai
    Ma, Wen-Qiang
    Yan, Zhi-Bo
    Zhang, Fu-Min
    Wang, Shao-Hua
    Tu, Yong-Qiang
    Zhang, Xiao-Ming
    Tian, Jin-Miao
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10099 - 10103
  • [7] Asymmetric iodine catalysis-mediated enantioselective oxidative transformations
    Claraz, Aurelie
    Masson, Geraldine
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (30) : 5386 - 5402
  • [8] Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole
    Dhineshkumar, Jayaraman
    Gadde, Karthik
    Prabhu, Kandikere Ramaiah
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) : 228 - 235
  • [9] Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine
    Ding, Ming
    Liang, Kangjiang
    Pan, Rui
    Zhang, Hongbin
    Xia, Chengfeng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) : 10309 - 10316
  • [10] Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant
    Dohi, T
    Maruyama, A
    Yoshimura, M
    Morimoto, K
    Tohma, H
    Kita, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6193 - 6196
123456