Furanmonogones A and B: two rearranged acylphloroglucinols with a 4,5-seco-3(2H)-furanone core from the flowers of Hypericum monogynum

被引：27
|
作者：
Xu, Wen-Jun [1 ]
Luo, Jun [1 ]
Li, Rui-Jun [1 ]
Yang, Ming-Hua [1 ]
Kong, Ling-Yi [1 ]
机构：
[1] China Pharmaceut Univ, Dept Nat Med Chem, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 02期
关键词：
POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; A-D; DERIVATIVES; STEREOCHEMISTRY; CHEMISTRY; SKELETON; ANALOGS;
D O I：
10.1039/c6qo00620e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Furanmonogones A (1) and B (2), two rearranged acylphloroglucinols with an unprecedented 4,5-seco-3(2H)-furanone skeleton, were isolated from the flowers of Hypericum monogynum. Their structures were established based on 1D- and 2D-NMR data, quantum chemical predictions (QCP) of C-13 NMR chemical shifts, and electronic circular dichroism (ECD) calculations. Baeyer-Villiger oxidation at the single bond (C4-C5) of the acylphloroglucinol core was proposed as a key step in the plausible biogenetic pathway of 1 and 2.
引用
收藏
页码：313 / 317
页数：5
相关论文
共 50 条
  • [21] STUDIES ON MECHANISM OF FORMATION OF 4-HYDROXY-5-METHYL-3(2H)-FURANONE, A COMPONENT OF BEEF FLAVOR, FROM AMADORI PRODUCTS
    HICKS, KB
    FEATHER, MS
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1975, 23 (05) : 957 - 960
  • [22] SYNTHESIS AND HERBICIDAL ACTIVITY OF THIAZOLO[4,5-B]PYRIDINE-3(2H)-ACETIC ACID-DERIVATIVES
    HEGDE, SG
    MAHONEY, MD
    JONES, CR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 106 - AGRO
  • [23] THIAZOLO[4,5-B]PYRIDINE-3(2H)-ACETIC ACID-DERIVATIVE - SYNTHESIS AND HERBICIDAL ACTIVITY
    HEGDE, SG
    MAHONEY, MD
    JONES, CR
    SYNTHESIS AND CHEMISTRY OF AGROCHEMICALS IV, 1995, 584 : 70 - 77
  • [24] Racemic 3,4-dihydro-4-naphthyl-naphthalen-1(2H)-ones from Juglans regia flowers
    Li, Qian
    Deng, An-Jun
    Ji, Ming
    Li, Zhi-Hong
    Chen, Xiao-Guang
    Qin, Hai-Lin
    FITOTERAPIA, 2019, 139
  • [25] ISOLATION OF 4-HYDROXY-2-(HYDROXYMETHYL)-5-METHYL-3(2H)-FURANONE FROM SUGAR AMINO-ACID REACTION MIXTURES
    HIEBL, J
    LEDL, F
    SEVERIN, T
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1987, 35 (06) : 990 - 993
  • [26] Thermolysis of 5-azido-4-arylpyridazin-3(2H)-ones:: An efficient and versatile synthesis of pyridazino[4,5-b]indoles
    Haider, Norbert
    Wobus, Andrea
    HETEROCYCLES, 2006, 68 (12) : 2549 - 2561
  • [27] ACTION OF ORGANOMETALLICS ON 2,2-DIALKOXY-3,4-DIHYDRO-(2H)-PYRANS AND 2-ETHOXY-CYCLOALKANO 4,5-B!3,4-DIHYDRO-(2H)-PYRANS
    THUY, VM
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, (11B): : 49 - &
  • [28] AN ENTRY TO 5,6,7,8-TETRAHYDRO-4-CINNOLONES FROM 4,5,6,7-TETRAHYDROBENZO-3(2H)-FURANONE DERIVATIVES
    GELIN, S
    DOLMAZON, R
    HETEROCYCLES, 1983, 20 (01) : 61 - 64
  • [29] Synthesis and chemiluminescence of 10-hydroxy and 10-aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones
    Tominaga, Y
    Yoshioka, N
    Kataoka, S
    Shigemitsu, Y
    Hirota, T
    Sasaki, K
    HETEROCYCLES, 1999, 50 (01) : 43 - 46
  • [30] Generation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone from Rhamnose as Affected by Reaction Parameters: Experimental Design Approach
    Illmann, Silke
    Davidek, Tomas
    Gouezec, Elisabeth
    Rytz, Andreas
    Schuchmann, Heike P.
    Blank, Imre
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (07) : 2889 - 2895
12345