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
  • [21] (+)-(1S,3S,6S,8S)-4,9-TWISTADIENE AND (-)-(1R,3R,6R,8R)-4,9-TWISTADIENE - SYNTHESIS AND ABSOLUTE-CONFIGURATION
    CAPRARO, HG
    GANTER, C
    HELVETICA CHIMICA ACTA, 1980, 63 (05) : 1347 - 1351
  • [22] An integrated chemoenzymatic synthesis of enantiopure (-)-(1R,5S)-cyclosarkomycin: A sarkomycin precursor
    Andrau, L
    Lebreton, J
    Viazzo, P
    Alphand, V
    Furstoss, R
    TETRAHEDRON LETTERS, 1997, 38 (05) : 825 - 826
  • [23] Synthesis of sterically hindered enantiopure (1S,2S,3R,5R)-neoisopinocampheyl aryl ethers by the Mitsunobu reaction
    Zhang, C
    Cen, YN
    Sun, ZM
    Shen, XM
    Deng, ZW
    SYNTHETIC COMMUNICATIONS, 2002, 32 (20) : 3127 - 3135
  • [24] SYNTHESIS OF (2R 4R,S)-DIMETHLYDOCOSANOIC AND (2S 4R,S)-DIMETHYLDOCOSANOIC ACIDS
    WALLACE, PA
    MINNIKIN, DE
    CHEMISTRY AND PHYSICS OF LIPIDS, 1994, 72 (01) : 87 - 101
  • [25] Synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyldocosane from Antitrogus parvulus via diastereoselective hydrogenations
    Zhou, Jianguang
    Zhu, Ye
    Burgess, Kevin
    ORGANIC LETTERS, 2007, 9 (07) : 1391 - 1393
  • [26] SYNTHESIS AND INVESTIGATION ON THE MODE OF ACTION OF (4R,5S)/(4S,5R)- AND (4R,5R)/(4S,5S)-2,4,5-TRIARYL-4,5-DIHYDRO-1H-IMIDAZOLE DERIVATIVES
    Elsner, Sabrina
    Gust, Ronald
    DRUGS OF THE FUTURE, 2009, 34 : 204 - 204
  • [27] CRYSTAL AND MOLECULAR-STRUCTURE OF (1S,3S,5R,7S,8R,9R)-9-PARA-BROMOBENZOYLOXY-1,4,4,8-TETRAMETHYLTRICYCLO[5.4.0.03,5]UNDECANE
    QUICK, A
    ROGERS, D
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (04): : 460 - 465
  • [28] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF 1R(S),3S(R),8R(S),10S(R)- AND 1S(R),3R(S),8R(S),10S(R)-3,5,7,7,10,12,14,14-OCTAMETHYL-1,4,8,11 TETRAAZACYCLOTETRADECA-4,11-DIENENICKEL(II) COMPLEXES
    ITO, T
    SOMA, K
    WATANABE, M
    CHEMISTRY LETTERS, 1976, (05) : 421 - 424
  • [29] Total Synthesis of (3S, 5R, 3′S, 5′R)-Capsorubin
    Frederico, Daniel
    Constantino, Mauricio G.
    Donate, Paulo M.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2009, 20 (05) : 888 - U148
  • [30] Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
    Tilekar, JN
    Patil, NT
    Jadhav, HS
    Dhavale, DD
    TETRAHEDRON, 2003, 59 (11) : 1873 - 1876