REGIOSELECTIVE SYNTHESIS OF 2,4-DIFFERENTIALLY ARYLATED PYRROLES AND ITS APPLICATION TO THE SYNTHESIS OF LAMELLARINS

被引：6
|
作者：
Fukuda, Tsutomu [1 ]
Anzai, Mizuho [1 ]
Iwao, Masatomo [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Engn, Div Chem & Mat Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
来源：
HETEROCYCLES | 2016年 / 93卷 / 02期
关键词：
ALPHA 20-SULFATE ANALOGS; G TRIMETHYL ETHER; BIOLOGICAL-ACTIVITY; CATALYZED TRANSANNULATION; ANTITUBERCULAR AGENTS; EFFICIENT SYNTHESIS; MODULAR SYNTHESIS; TERMINAL ALKYNES; DERIVATIVES; ALKALOIDS;
D O I：
10.3987/COM-15-S(T)49
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 2,4-differentially arylated pyrroles has been developed via stepwise palladium-catalyzed Suzuki-Miyaura coupling of N-benzenesulfonyl-4-bromo-2-iodopyrrole with different arylboronic acids. This method has been applied to the new synthesis of the marine natural products lamellarins.
引用
收藏
页码：593 / 612
页数：20
相关论文
共 50 条
  • [31] Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
    Wang, Sibin
    Zhelavskyi, Oleksii
    Lee, Jeonghyo
    Arguelles, Alonso J.
    Khomutnyk, Yaroslav Ya
    Mensah, Enoch
    Guo, Hao
    Hourani, Rami
    Zimmerman, Paul M.
    Nagorny, Pavel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (44) : 18592 - 18604
  • [32] SYNTHESIS OF 2,4-DIPHENYLBUTYL 2,4-DIPHENYLBUTYRATE AND ITS APPLICATION TO A PLASTICIZER FOR POLYVINYL-CHLORIDE)
    SAIDO, K
    KUROKI, T
    IKEMURA, T
    KIRISAWA, M
    NIPPON KAGAKU KAISHI, 1983, (10) : 1531 - 1534
  • [33] THE SYNTHESIS OF AROMATIC LEUKOTRIENE ANALOGS - REGIOSELECTIVE TRAPPING OF 2,4'-DILITHIOPHENYLETHYNE
    FURBER, M
    TAYLOR, RJK
    BURFORD, SC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07): : 1573 - 1578
  • [34] Facile synthesis of 2-alkyl/aryloxy-2H-azirines and their application in the synthesis of pyrroles
    Qi, Xinxin
    Xu, Xianxiu
    Park, Cheol-Min
    CHEMICAL COMMUNICATIONS, 2012, 48 (33) : 3996 - 3998
  • [35] Regioselective Synthesis of 2,5-Disubstituted Pyrroles via Stepwise Iododesilylation and Coupling Reactions
    Yu, Qixin
    Li, Xiaoyu
    Wang, Xinyue
    Liu, Jianhui
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2018, 71 (2-3) : 95 - 101
  • [36] REGIOSELECTIVE PHOTOADDITION OF PYRROLES AND ALIPHATIC CARBONYL-COMPOUNDS - NEW SYNTHESIS OF 3(4)-SUBSTITUTED PYRROLES
    JONES, G
    GILOW, HM
    LOW, J
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16): : 2949 - 2951
  • [37] Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles:: A formal total synthesis of lukianol A
    Liu, JH
    Yang, QC
    Mak, TCW
    Wong, HNC
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3587 - 3595
  • [38] HIGHLY STEREOSELECTIVE AND REGIOSELECTIVE ALKYLATION OF ALKYLIDENEMALONATES - ITS APPLICATION TO THE SYNTHESIS OF (+/-)-CANADENSOLIDE
    TSUBOI, S
    MURANAKA, K
    SAKAI, T
    TAKEDA, A
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25): : 4944 - 4946
  • [39] SYNTHESIS OF 2,4-OXAZOLIDINEDIONE AND ITS DERIVATIVES
    KOBAYASHI, M
    KITAZAWA, M
    SAITO, T
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1983, 103 (11): : 1195 - 1199
  • [40] SYNTHESIS OF 2,4-DIAMINOSTYRENE AND ITS DERIVATIVES
    SINYAVSK.VG
    KORNIENK.RA
    UKRAINSKII KHIMICHESKII ZHURNAL, 1972, 38 (01): : 52 - &
12345