Synthesis of enantiomerically pure carbohydrate-derived annulated cyclopentadienes and of a ferrocene

被引：3
|
作者：
Widauer, C [1 ]
Bernet, B [1 ]
Vasella, A [1 ]
机构：
[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
来源：
SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 04期
关键词：
D O I：
10.1080/00397919808005930
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3,4,6-Tetra-O-methyl-D-mannitol (3) was synthesized on a large scale in five steps from D-mannitol. Its dimesylate 4 reacted with cyclopentadienyl-sodium to the spiro[4,4]nona-1,3-diene 5. Thermolysis of 5 at 180 degrees gave a mixture of the three tetrahydroindenes 6a/6b/6c which were transformed into the ferrocene 7. The structure of 7 was established by X-ray analysis.
引用
收藏
页码：593 / 602
页数：10
相关论文
共 50 条
  • [21] First synthesis of a carbohydrate-derived pyridyl bis(thiazoline) ligand
    Irmak, Mustafa
    Lehnert, Tobias
    Boysen, Mike M. K.
    TETRAHEDRON LETTERS, 2007, 48 (44) : 7890 - 7893
  • [22] Synthesis of an enantiomerically pure serine-derived thiazole
    Sowinski, JA
    Toogood, PL
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22): : 7671 - 7676
  • [23] Practical synthesis of enantiomerically pure 2-(diphenylphosphanyl)ferrocene carboxylic acid
    Breit, B
    Breuninger, D
    SYNTHESIS-STUTTGART, 2005, (16): : 2782 - 2786
  • [24] Simple Carbohydrate-Derived Multifunctional Gels
    Mitra, Ankita
    Sarkar, Vikramjit
    Mukhopadhyay, Balaram
    CHEMISTRYSELECT, 2017, 2 (31): : 9958 - 9961
  • [25] Synthesis and Metal Complexes of Thiourea Ligands Containing Carbohydrate-Derived Substituents
    Sternberg, Michelle
    Rust, Joerg
    Lehmann, Christian W.
    Mohr, Fabian
    HELVETICA CHIMICA ACTA, 2013, 96 (02) : 280 - 288
  • [26] Advances in the synthesis of antiviral agents from carbohydrate-derived chiral pools
    Sharma, Anjali
    Bera, Smritilekha
    Mondal, Dhananjoy
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2023, 41 (7-9) : 424 - 510
  • [27] APPROACHES TO SOME CARBOHYDRATE-DERIVED SULTONES
    FRASERREID, B
    SUN, KM
    TSANG, RYK
    SINAY, P
    PIETRASZKIEWICZ, M
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02): : 260 - 263
  • [28] Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions
    Shen, Chao
    Liao, Hanxiao
    Shen, Fangyi
    Zhang, Pengfei
    CATALYSIS COMMUNICATIONS, 2013, 41 : 106 - 109
  • [29] THE SYNTHESIS OF SOME CARBOHYDRATE-DERIVED PRECURSORS TO TYLONOLIDE, THE AGLYCON OF THE ANTIBIOTIC TYLOSIN
    HUGHES, AB
    STICK, RV
    TILBROOK, DMG
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (10) : 1681 - 1695
  • [30] Diastereoselective aza-Michael addition for synthesis of carbohydrate-derived spiropiperazinones
    Jevgeņija Lugiņina
    Deniss Vasiļjevs
    Ilgvalds Ivanovs
    Anatoly Mishnev
    Māris Turks
    Monatshefte für Chemie - Chemical Monthly, 2019, 150 : 21 - 28
12345