Asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one

被引：1
|
作者：
Shi, XX
He, W
Wu, QQ
Yin, J
Ni, F
Jin, XZ
机构：
[1] E China Univ Sci & Technol, Fac Chem & Pharmaceut Engn, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 15期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/j.tetasy.2004.06.016
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The asymmetric synthesis of (1S,6R,7S,9R)-7,9-bis(tert-butyldiphenylsilyloxy)-3-oxabicyclo[4,3,0]nonan-2-one 1 from (4S)-4-acetoxy-2-methoxycarbonyl-3-methoxycarbonylmethyl-2-cyclopenten-1-one 2 is described in eight steps. Compound 2 was readily prepared from L-malic acid according to a known procedure. The key step of this synthesis is a palladium on charcoal catalyzed hydrogenation of olefinic bicyclic lactone 9. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2327 / 2331
页数：5
相关论文
共 50 条
  • [41] ALKYLATION OF (1S,2R,5R,6S,7R)- AND (1R,2R,5R,6S,7S)-5-METHYL-4-OXATRICYCLO-[5.2.1.0/2,6]-8-DECEN-3-ONE - APPLICATION TO THE SYNTHESIS OF (R)-3-ALKYL-5-METHYL-2(5H)-FURANONES
    CORBERA, J
    FONT, J
    MONSALVATJE, M
    ORTUNO, RM
    SANCHEZFERRANDO, F
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18): : 4393 - 4395
  • [42] Preparation of 3,125I-benzyl-(6R,7S)-7-methoxy-3-acetoxymethyl-3-cephem-4-carboxamide-1,1 -dioxide
    Synthetic Chemistry Department, Radiosynthesis Section, 709 Swedeland Road, King of Prussia, PA 19406-0939, United States
    不详
    J. Label. Compd. Radiopharm., 1 (77-81):
  • [43] Crystal structure of (1S,3S,6S,7S,8S,9R)-7,9-dihydroxy-6-(4-methoxybenzyl)3-[N-methyl-N-(4-methylphenyl)suffonylamino]-5-azatricyclo[6.3.1.01.5] dodecan-4-one-water (1/1),C27H34N2O6S • H2O
    Ousmer, M
    Braun, NA
    Ciufolini, MA
    Perrin, A
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2001, 216 (04): : 621 - 622
  • [44] Crystal structure of tert-butyl (+)-(1S,5R,6R,7S,8R,4'S)-8-hydroxy-6-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-oxobicyclo[3.2.1]octane-7-carboxylate, C18H28O6
    Peters, K
    Peters, EM
    Braun, NA
    Spitzner, D
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1996, 211 (12): : 961 - 962
  • [45] SYNTHESIS OF 3-FUNCTIONALIZED CEPHALOSPORINS BY PHOTOINITIATED BROMINATION - TRANSFORMATIONS OF 2,2,2-TRICHLOROETHYL 1S,6R,7R)-3-BROMOMETHYL-7-FORMAMIDOCEPH-3-EM-4-CARBOXYLATE, 1-OXIDE
    COWLEY, BR
    HUMBER, DC
    LAUNDON, B
    LONG, AG
    LYND, AL
    TETRAHEDRON, 1983, 39 (03) : 461 - 467
  • [46] Synthesis of mono- and sesquiterpenoids .25. Synthesis of (6R*,7R*)-7-hydroxy-6,11-cyclofarnes-3(15)-en-2-one, the racemate of the antibacterial sesquiterpene from Premna oligotricha, and its (6R*,7S*) isomer
    Yajima, A
    Takikawa, H
    Mori, K
    LIEBIGS ANNALEN, 1996, (06): : 891 - 897
  • [47] (1S,3R,8S,9R,10S)-2,2-Dichloro-3,7,7,10-tetramethyl-9,10-epoxytricyclo[6.4.0.01,3]dodecane
    Benharref, Ahmed
    El Ammari, Lahcen
    Avignant, Daniel
    Oudahmane, Abdelghani
    Berraho, Moha
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3125 - U220
  • [48] (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9 beta,10 beta-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]-dodecane
    Oukhrib, Abdelouahd
    Benharref, Ahmed
    Saadi, Mohamed
    Berraho, Moha
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O521 - +
  • [49] Synthesis of (±)-leucomalure [(3Z,6R*,7S*,9R*,10S*)-cis-6,7-cis-9,10-diepoxy-3-henicosene], the major components of the female sex pheromone of the satin moth
    Lizarraga, JR
    Mori, K
    NATURAL PRODUCT LETTERS, 2001, 15 (02): : 89 - 92
  • [50] 5R, 6R, 7R, 9R, 13R, 14S)-21-cyclopropylmethyl-6,14-endo-ethano-2′,3′,4′,5′,7,8-hexahydro-4′,4′,5′,5′-tetramethylfurano[2′,3′6,7]normorphide hydrochloride methanol solvate
    Cejka, J
    Kratochvíl, B
    Chudík, M
    Jegorov, A
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2274 - O2276
12345