The synthesis of (4S,5S)-(-)-isocytoxazone

被引:4
作者
Rozwadowska, Maria D. [1 ]
Tomczak, Anna [1 ]
机构
[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland
关键词
STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; CYTOKINE MODULATOR; CYTOXAZONE; ALCOHOLS;
D O I
10.1016/j.tetasy.2009.07.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(4S,5S)-(-)-Isocytoxazone, which is needed for a configurational study, was synthesized from the commercially available (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediolin which the p-nitro substituent was replaced by a p-methoxyl group; the thus prepared p-methoxyphenyl amino diol was cyclized via an N-Boc derivative. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2048 / 2051
页数:4
相关论文
共 50 条
[31]   Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum [J].
Jimenez-Teja, Daniel ;
Daoubi, Mourad ;
Collado, Isidro G. ;
Hernandez-Galan, Rosario .
TETRAHEDRON, 2009, 65 (17) :3392-3396
[32]   Synthesis of (4S,6S)-4-hydroxy-1,7-dioxaspiro[5.5]undecane, a component of the olive fruit fly pheromone, by employing a novel asymmetric oxy-Michael addition [J].
Watanabe, H ;
Itoh, D ;
Kitahara, T .
SYNTHESIS-STUTTGART, 2000, (13) :1925-1929
[33]   Revisiting Vibrational Circular Dichroism Spectra of (S)-(+)-Carvone and (1S,2R,5S)-(+)-Menthol Using SimIR/VCD Method [J].
Shen, Jian ;
Li, Yi ;
Vaz, Roy ;
Izumi, Hiroshi .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2012, 8 (08) :2762-2768
[34]   Straightforward Approach to the Discrimination of (4R)- and (4S)β-Isocryptoxanthin from a Conformationally Insensitive CD Band [J].
Hosoi, Shinzo ;
Tanaka, Takeyuki ;
Katsumoto, Yukiteru ;
Maoka, Takashi ;
Fujiwara, Toshio ;
Yamashita, Masayuki ;
Node, Manabu .
NATURAL PRODUCT COMMUNICATIONS, 2010, 5 (11) :1733-1736
[35]   A Short and Efficient Asymmetric Synthesis of (±)-epi-Cytoxazone from cis-(1R,2S,5R)-Menthyl 4-Methoxyphenylglycidates [J].
Er, Mustafa ;
Coskun, Necdet .
CHEMISTRY OF NATURAL COMPOUNDS, 2014, 50 (06) :1071-1074
[36]   Synthesis of Orthogonally Protected (2R, 3R, 4S)-4-Amino-2,3-dihydroxyheptane-1,7-dioic Acid [J].
Tokairin, Yoshinori ;
Maita, Kakeru ;
Takeda, Sho ;
Konno, Hiroyuki .
SYNTHESIS-STUTTGART, 2015, 47 (03) :351-358
[37]   Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(-)-myrtenol nitrate [J].
Bew, Sean P. ;
Hiatt-Gipson, Glyn D. ;
Mills, Graham P. ;
Reeves, Claire E. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 :1081-1095
[38]   Enantioselective approach to tropane skeleton: Synthesis of (1S,5S,6R)-6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-one [J].
Pollini, GP ;
De Risi, C ;
Lumento, F ;
Marchetti, P ;
Zanirato, V .
SYNLETT, 2005, (01) :164-166
[39]   X-ray diffraction structure of (5S)-3,4-dichloro-5-menthoxy-2(5H)-furanone [J].
Bott, SG ;
Yang, KY ;
Richmond, MG .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2003, 33 (07) :585-588
[40]   X-ray diffraction structure of (5S)-3,4-dichloro-5-menthoxy-2(5H)-furanone [J].
Simon G. Bott ;
Kaiyuan Yang ;
Michael G. Richmond .
Journal of Chemical Crystallography, 2003, 33 :585-588