BF3•Et2O-Mediated annulation of α-keto acids with aliphatic ketones for the synthesis of γ-hydroxy-butenolides and γ-alkylidene-butenolides

被引:5
|
作者
Cheng, Zhenfeng [1 ]
Gu, Qingyun [1 ]
Xie, Yushan [1 ]
Zhang, Yanan [1 ]
Zeng, Xiaobao [1 ]
机构
[1] Nantong Univ, Sch Pharm, Nantong 226001, Peoples R China
关键词
DECARBOXYLATIVE ACYLATION; SUBSTITUTED BUTENOLIDES; SESQUITERPENE LACTONES; ALKYNES; ROOTS; ROUTE;
D O I
10.1039/d2ra04546j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Annulation reaction of alpha-keto acids with cyclic or acyclic aliphatic ketones is reported herein to divergently access gamma-hydroxy-butenolides and gamma-alkylidene-butenolides depending on the amount of BF3 center dot Et2O. This protocol features good functional tolerance and ease of operation, to open a route to access butenolides via an annulation and dehydration process.
引用
收藏
页码:24237 / 24241
页数:5
相关论文
共 30 条
  • [1] TiCl4-n-Bu3N-mediated cascade annulation of ketones with α-ketoesters: a facile synthesis of highly substituted fused γ-alkylidene-butenolides
    Palange, Megha N.
    Gonnade, Rajesh G.
    Kontham, Ravindar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (23) : 5749 - 5759
  • [2] BF3•Et2O-mediated cascade cyclizations:: Synthesis of schweinfurthins F and G
    Mente, Nolan R.
    Neighbors, Jeffrey D.
    Wiemer, David F.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20): : 7963 - 7970
  • [3] Synthesis of Spirolactones via a BF3•Et2O-Promoted Cascade Annulation of α-Keto Acids and 1,3-Enynes
    Zhao, Beibei
    Zhang, Zhen
    Li, Pinhua
    Miao, Tao
    Wang, Lei
    ORGANIC LETTERS, 2021, 23 (15) : 5698 - 5702
  • [4] BF3•Et2O-mediated intramolecular cyclization of unsaturated amides: convenient synthesis of dihydroquinolin-2-one-BF2 complexes
    Liu, Xu
    Zhang, Qian
    Xin, Xiaoqing
    Zhang, Rui
    Zhang, Ning
    Liang, Yongjiu
    Dong, Dewen
    RSC ADVANCES, 2014, 4 (68) : 36234 - 36240
  • [5] BF3 • Et2O-Mediated Annulation of 2-Alkynyl Biaryls with N-(Arylthio) Succinimides: An Efficient Approach to Access 9-Sulfenylphenanthrenes
    Jin, Haoru
    Zhou, Chao
    Li, Hongji
    Li, Pinhua
    Wang, Lei
    Miao, Tao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (38)
  • [6] Synthesis of 3-Sulfenylated Coumarins: BF3•Et2O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides
    Gao, Wen-Chao
    Liu, Tao
    Zhang, Bing
    Li, Xing
    Wei, Wen-Long
    Liu, Qiang
    Tian, Jun
    Chang, Hong-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11297 - 11304
  • [7] Facile synthesis of complicated 9,9-diarylfluorenes based on BF3•Et2O-mediated Friedel-Crafts reaction
    Xie, Ling-Hai
    Hou, Xiao-Ya
    Hua, Yu-Ran
    Tang, Chao
    Liu, Feng
    Fan, Qu-Li
    Huang, Wei
    ORGANIC LETTERS, 2006, 8 (17) : 3701 - 3704
  • [8] Studies on flavans.: 1.: Facile synthesis of (±)-7-hydroxy-3′,4′-methylenedioxyflavan and (±)-4′-hydroxy-7-methoxyflavan by a BF3•Et2O-mediated pyran cyclization
    Li, Y
    Yang, JH
    Li, WDZ
    Hou, LM
    Xue, JJ
    Li, YL
    JOURNAL OF NATURAL PRODUCTS, 2001, 64 (02): : 214 - 216
  • [9] A Simple BF3•Et2O-mediated Cycloaddition Reaction to the Formation of Cyclic Monoterpenoid Pyrano[3,2-a]carbazole Alkaloids
    Tan, Siow-Ping
    Nafiah, Mohd Azlan
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (05) : 395 - 399
  • [10] Synthesis of naphthalene derivatives through inexpensive BF3·Et2O-catalyzed annulation reaction of arylacetaldehydes with arylalkynes
    XIANG ShiKai
    HU Hao
    MA Jing
    LI YuanZhuo
    WANG BiQin
    FENG Chun
    ZHAO KeQing
    HU Ping
    CHEN XiaoZhen
    Science China(Chemistry), 2013, 56 (07) : 945 - 960