Synthesis of enantiopure (S,R,S)- and (R,S,R)-1,4,5,8,9,16-hexa-hydroxytetraphenylenes

被引:33
|
作者
Wu, An-Hui
Hau, Chun-Kit
Wong, Henry N. C. [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Ctr Novel Funct Mol, Shatin, Hong Kong, Peoples R China
[2] Chinese Univ Hong Kong, Cent Lab, Inst Mol Technol Drug Discovery & Synth, Area Excellence,Univ Grants Comm Hong Kong, Shatin, Hong Kong, Peoples R China
关键词
demethylation; hypervalent compounds; iodobenzene diacetate; phenolic oxidation; quinone; resolution;
D O I
10.1002/adsc.200600499
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
114,51819,16-Hexahydroxytetraphenylene (5) was synthesized by an iodobenzene diacetate-mediated phenolic oxidation. Enantiopure forms of 1,4,5,8,9,16-hexahydroxytetraphenylenes [(S,R,S)-5 and (R,S,R)] were successfully synthesized either by using (S,S)-and (R,R)-1,8,9,16-tetramethoxytetraphenylenes [(SS)-7 and (R,R)-7] as starting materials or by direct resolution of 1,4,5,8,9,16-hexahydroxytetraphenylene (5).
引用
收藏
页码:601 / 608
页数:8
相关论文
共 50 条
  • [31] Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
    Chakraborty, C
    Dhavale, DD
    CARBOHYDRATE RESEARCH, 2006, 341 (07) : 912 - 917
  • [32] S1-S2+R, S1+R-S2+R paradigm and schizophrenia
    Numakura, K
    Kato, M
    Totsuka, S
    Yamamoto, T
    RECENT ADVANCES IN EVENT-RELATED BRAIN POTENTIAL RESEARCH, 1996, 1099 : 905 - 907
  • [33] Synthesis and anthelmintic activity of cyclohexadepsipeptides with (S,S,S,R,S,R)-configuration
    Jeschke, P
    Benet-Buchholz, J
    Harder, A
    Etzel, W
    Schindler, M
    Thielking, G
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) : 3285 - 3288
  • [34] KINETIC STUDY OF THE REACTION OF THE 5,5,7R(S),12,12,14R(S)-HEXAMETHYL-1S(R),4S(R),8S(R),11S(R)-TETRAAZACYCLOTETRADECANENICKEL(II) ION AND DIMETHYLSULFOXIDE INVOLVING A SINGLET-TRIPLET SPIN-STATE EQUILIBRIUM
    MASUDA, Y
    ENDO, N
    ITO, T
    YOSHIDA, N
    FUJIMOTO, M
    CHEMISTRY LETTERS, 1979, (05) : 565 - 568
  • [35] OXIDATION-PRODUCTS OF ARACHIDONIC-ACID .3. THE SYNTHESIS OF METHYL 8R,9R,11R, 8S,9R,11R, AND 8S,9S,11R-TRIACETOXYEICOSA-5Z,12E,14Z-TRIENOATE
    JUST, G
    LUTHE, C
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (21): : 2286 - 2294
  • [36] Total synthesis of (8'R)- and (8'S)-corossoline
    Makabe, H
    Tanimoto, H
    Tanaka, A
    Oritani, T
    HETEROCYCLES, 1996, 43 (10) : 2229 - 2248
  • [37] STEREOCHEMICAL CORRELATIONS BETWEEN (2R,4'R,8'R)-ALPHA-TOCOPHEROL, (25S,26)-DIHYDROXYCHOLECALCIFEROL, (-)-(1S,5R)-FRONTALIN AND (-)-(R)-LINALOL
    BARNER, R
    HUBSCHER, J
    HELVETICA CHIMICA ACTA, 1983, 66 (03) : 880 - 890
  • [38] A total synthesis of the (5R,8S,13R,16S)-isomer of pyrenophorol
    Amigoni, S
    LeFloch, Y
    TETRAHEDRON-ASYMMETRY, 1997, 8 (16) : 2827 - 2831
  • [39] Synthesis and Crystal Structure of (1R,2S,5R,8S,9R,10S)-8-Methyl-4-aza-5-phenyl-7-oxatetracyclo[8.2.1.02,9.04,8]-11-en-3-one
    Ye, JL
    Wei, ZB
    Chen, Z
    Huang, PQ
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2003, 22 (02) : 228 - 232
  • [40] Stereoselective total synthesis of (-)-(5S,8R,13S,16R)-pyrenophorol
    Edukondalu, Perugu
    Sreenivasulu, Reddymasu
    Chiranjeevi, Barreddi
    Kumar, Vuppula Naresh
    Raju, Rudraraju Ramesh
    MONATSHEFTE FUR CHEMIE, 2015, 146 (08): : 1309 - 1314