Asymmetric Michael-Aldol Tandem Reaction of 2-Substituted Benzofuran-3-ones and Enones: A Facile Synthesis of Griseofulvin Analogues

被引：43
|
作者：
Dong, Nan [1 ]
Li, Xin [1 ]
Wang, Feng [1 ]
Cheng, Jin-Pei [1 ]
机构：
[1] Nankai Univ, Dept Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 18期
基金：
中国国家自然科学基金;
关键词：
3-SUBSTITUTED BENZOFURAN-2(3H)-ONES; CHEMICAL STRUCTURE; ADDITION-REACTIONS; DL-GRISEOFULVIN; ORAL TREATMENT; ANTIBIOTICS; DERIVATIVES; RINGWORM;
D O I：
10.1021/ol402346c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective Michael aldol tandem reaction with respect to prochiral 2-substituted benzofuran-3-ones and enones by a facile primary amine catalyst was investigated. The approach provides rapid access to the desired pharmaceutically active griseofulvin analogues.
引用
收藏
页码：4896 / 4899
页数：4
相关论文
共 50 条
  • [31] Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea
    Li, Xin
    Xue, Xiao-Song
    Liu, Cong
    Wang, Bin
    Tan, Bo-Xuan
    Jin, Jia-Lu
    Zhang, Yue-Yan
    Dong, Nan
    Cheng, Jin-Pei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (02) : 413 - 420
  • [32] Asymmetric Synthesis of 2-Substituted Hexahydroquinolin-4-ones Using a Pd-Catalyzed Asymmetric Allylic Amination and Intramolecular Mannich Reaction: Catalytic Asymmetric Synthesis of 2-epi-cis-195A
    Kakugawa, Kazumi
    Nemoto, Tetsuhiro
    Kohno, Yuta
    Hamada, Yasumasa
    SYNTHESIS-STUTTGART, 2011, (16): : 2540 - 2548
  • [33] New efficient synthesis of 2-substituted benzothieno[3,2-d]pyrimidin-4(3H)-ones via a tandem aza-Wittig reaction
    Xu, Sheng-Zhen
    Hu, Yang-Gen
    Ding, Ming-Wu
    SYNTHESIS-STUTTGART, 2006, (24): : 4180 - 4186
  • [34] A facile synthesis of 2-amino-3H-quinazolin-4-ones with tandem Aza-Wittig reaction.
    Ding, MW
    Zeng, GP
    Wu, TJ
    SYNTHETIC COMMUNICATIONS, 2000, 30 (09) : 1599 - 1604
  • [35] Synthesis of 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones by a Michael-type tandem reaction
    Syha, Yvonne
    Valmalle, Charlene
    Bats, Jan W.
    Kock, Michael
    Abdel-Tawab, Mona
    Schubert-Zsilavecz, Manfred
    MONATSHEFTE FUR CHEMIE, 2006, 137 (10): : 1357 - 1364
  • [36] Synthesis of 2,3-Dihydrothiazolo[3,2-a]pyrimidin-5-ones by a Michael-type Tandem Reaction
    Yvonne Syha
    Charlene Valmalle
    Jan W. Bats
    Michael Kock
    Mona Abdel-Tawab
    Manfred Schubert-Zsilavecz
    Monatshefte für Chemie / Chemical Monthly, 2006, 137 : 1357 - 1364
  • [37] Organic Catalytic Oxa-Michael-Aldol Cascade Reaction for the Asymmetric Synthesis of (R)-2-Phenyl-2H-chromene-3-carbaldehyde
    Li, Chonglong
    Chen, Chaoxing
    Zhan, Murong
    Wang, Zixuan
    Wang, Shuyi
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (SUPPL1) : S140 - S146
  • [38] Reaction of anthranilic acid with orthoesters: a new facile one-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones
    Khajavi, MS
    Montazari, N
    Hosseini, SSS
    JOURNAL OF CHEMICAL RESEARCH-S, 1997, (08): : 286 - 287
  • [39] A novel and efficient synthesis of 2-substituted quinazolin-4(3H)-ones by the reaction of (het)arylmethanamines with isatoic anhydride
    Mahdavi, Mohammad
    Hassanzadeh, Rasool
    Soheilizad, Mehdi
    Golshani, Shiva
    Moghimi, Setareh
    Firoozpour, Loghman
    Shafiee, Abbas
    Foroumadi, Alireza
    TETRAHEDRON LETTERS, 2016, 57 (33) : 3770 - 3772
  • [40] ENANTIOSELECTIVE SYNTHESIS OF 2,2-DIALKYLTETRAHYDROPYRAN-3-ONES VIA THE ASYMMETRIC MICHAEL ADDITION-REACTION USING CHIRAL IMINES
    DESMAELE, D
    PAIN, G
    DANGELO, J
    TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 863 - 866
12345