Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate

被引:5
|
作者
Torosyan, S. A. [1 ]
Gimalova, F. A. [1 ]
Valeev, R. F. [1 ]
Miftakhov, M. S. [1 ]
机构
[1] Russian Acad Sci, Inst Organ Chem, Ufa Sci Ctr, Ufa 450054, Russia
关键词
ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; ALCOHOLS; EFFICIENT;
D O I
10.1134/S1070428011050058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl)methanol epimeric at the C(7) atom resulted in scalemic (5R)-5-acetyl-2-methylcyclohex-2-en-1-one.
引用
收藏
页码:682 / 686
页数:5
相关论文
共 50 条
  • [31] Crystal structure of (1R,4S,5R,7R)-4-bromomethyl-4-methyl-3,6,8-trioxa-2-oxo-bicyclo[3.2.1]octane-7-dimethylcarboxamide, C10H14BrNO5
    Peters, K
    Peters, EM
    vonSchnering, HG
    Kuhn, B
    Jager, V
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1996, 211 (04): : 269 - 270
  • [32] Syntheses with organoboranes -: VIII.: Transformation of (1S,6R)-(+)-2-carene into (1S,6R)-(+)-3(10)-carene and (1R,5R)-(-)-α-thujene into (1R,5R)-(+)-sabinene
    Zaidlewicz, M
    Gimiñska, M
    TETRAHEDRON-ASYMMETRY, 1997, 8 (23) : 3847 - 3850
  • [33] Molecular and crystal structures of (6R,7R,14S)-6,14-etheno-7-[(1R)-1-hydroxyethyl]- and (6R,7R,14S)-6,14-etheno-7-[(1S)-1-hydroxyethyl]-6,7,8,14-tetrahydro-17-nor-17-phenylthebaine
    Bakhanova, IV
    Nesterov, VN
    Moiseev, SK
    Schmidhammer, H
    Kalinin, VN
    RUSSIAN CHEMICAL BULLETIN, 1998, 47 (11) : 2177 - 2181
  • [34] (1S,2R,4R,5R)-tert-Butyl N-(4-hydroxymethyl-6-oxabicyclo[3.1.0.]hex-2-yl)carbamate
    von Meltzer, M
    Marsch, M
    Carell, T
    Harms, K
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O23 - O24
  • [35] (+)-(1S,5R,6R)-6-[(S)-1-Hydroxy-2-(methoxymethyloxy)ethyl]-1-methyl-3-trichloromethyl-2-aza-4,7-dioxabicyclo-[3.3.0]oct-2-en-8-one
    Oishi, Takeshi
    Oishi, Hiroki
    Tsuzaki, Syun
    Sato, Takaaki
    Chida, Noritaka
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3185 - +
  • [36] Enantiomerically pure (1S,5R) and racemic 3-(1-benzothiophen-2-yl)-8-azoniabicyclo[3.2.1]oct-2-ene acetate
    Frostrup, Brian
    Peters, Dan
    Bond, Andrew D.
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2012, 68 : O298 - +
  • [37] Efficient syntheses of 13C-labelled erythromycin biosynthetic intermediates.: 2: (2S,3S,4S,5R,6R,7R)-3,6,7-trihydroxy-2,4,6-trimethyl-[1-13C]nonan-5-olide and S-2-acetylaminoethyl (2R,3S,4S,5R,6S,7R)-3,5,6,7-tetrahydroxy-2,4,6-trimethyl[1-13C]nonanethioate
    Iida, Katsum
    Kajiwara, Masahiro
    Fukui, Mineo
    Nakata, Tadashi
    Oishi, Takeshi
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2008, 51 (5-6): : 218 - 225
  • [38] STEREOSPECIFIC SYNTHESIS AND ANTIVIRAL PROPERTIES OF DIFFERENT ENANTIOMERICALLY PURE CARBOCYCLIC 2'-DEOXYRIBONUCLEOSIDE ANALOGS DERIVED FROM COMMON CHIRAL POOLS - (+)-(1R,5S)-2-OXABICYCLO[3.3.0]OCT-6-EN-3-ONE AND (-)-(1S,5R)-2-OXABICYCLO[3.3.0]OCT-6-EN-3-ONE
    BERES, J
    SAGI, G
    TOMOSKOZI, I
    GRUBER, L
    BAITZGACS, E
    OTVOS, L
    DECLERCQ, E
    JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) : 1353 - 1360
  • [39] A facile synthesis of (1S,5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol
    Tanaka, Takanori
    Tan, Qitao
    Iwanaga, Kazunari
    Hayashi, Masahiko
    CARBOHYDRATE RESEARCH, 2011, 346 (02) : 340 - 342
  • [40] Enantiospecific synthesis of [7R,6S,5S,4R]-triacetoxy-(-)-goniotriol
    Srikanth, GSC
    Krishna, UM
    Trivedi, GK
    TETRAHEDRON LETTERS, 2002, 43 (31) : 5471 - 5473