(2R,3R,5R)-2-[(2R,3aS,6aR)-2,3,3a,-4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-5-isopropenyl-2,3-dimethylcyclo-hexanone and (4aR,5S,7R)-5-isopropenyl-7,8,8-trimethyl-2,3,4,4a,-5,6,7,8-octahydronaphthalene-4a-carbonitrile

被引:4
|
作者
Ellis, DD [1 ]
Spek, AL [1 ]
机构
[1] Univ Utrecht, Bijvoet Ctr Biomol Res, Dept Crystal & Struct Chem, NL-3584 CH Utrecht, Netherlands
关键词
D O I
10.1107/S0108270100008805
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The molecular structures of two chiral cyclohexanones based on R-(-)-carvone, C17H26O3, (I), and C17H23NO, (II), are reported here. The six-membered ring in (I) is in a chair conformation with the two fused five-membered rings of the furofuranyl substituent in a cis configuration. Compound (II) contains a decalin group; one ring has the chair form whilst the other is in a half-boat conformation. Both products have been characterized spectroscopically, however, neither NMR nor IR results could prove the stereochemistry at each chiral centre unambiguously. The crystal analyses were used to examine conformational properties of the compounds.
引用
收藏
页码:1173 / 1175
页数:3
相关论文
共 50 条
  • [21] Synthesis of (±)-2R,4R,5S-2-methoxy-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexanone and (±)-2R,4S,5R-2-methoxy-5-nitro-4-(2,3,4-trimethoxyphenyl)cyclohexanone as colchicine mimetics
    Evans, KA
    Beshah, K
    Young, DH
    Fujimoto, TT
    Tice, CM
    Michelotti, EL
    TETRAHEDRON, 2003, 59 (13) : 2223 - 2229
  • [22] 4,4 '-[(2R*,3R*,4R*,5R*)-3,4-Dimethyltetrahydrofuran-2,5-diyl]diphenol
    de Jesus Favela-Hernandez, Juan Manuel
    Camacho-Corona, Maria del Rayo
    Bernes, Sylvain
    Flores-Alamo, Marcos
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3019 - +
  • [23] First stereoselective total synthesis of (3R, 3aS, 6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl-carbamate (diastereomer of Darunavir)
    Babu, Kilaru Ravendra
    Rao, Valasani Koteswara
    Sudhakar, Yellapu
    Raju, Chamarthi Naga
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (06): : 849 - 854
  • [24] [1R,2R,5(1')S,9R,2'R,4'R,5'S]-2,10,10-TRIMETHYL-3-OXA-6-AZATRICYCLO[7,1,1,0(2,7)]UNDECA-5-SPIRO[1'(2',4',5'-TRIMETHYLCYCLOHEXANE)]-6-ENE-4-ONE
    CHIARONI, A
    RICHE, C
    LAVERGNE, JP
    SADOUNE, M
    VIALLEFONT, P
    VIDAL, Y
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1994, 50 : 1122 - 1124
  • [25] The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers
    Kulkarni, Mukund G.
    Shaikh, Yunnus B.
    Borhade, Ajit S.
    Dhondge, Attrimuni P.
    Chavhan, Sanjay W.
    Desai, Mayur P.
    Birhade, Deekshaputra R.
    Dhatrak, Nagorao R.
    Gannimani, Ramesh
    TETRAHEDRON-ASYMMETRY, 2010, 21 (19) : 2394 - 2398
  • [26] [(2R,5S)-2,5-Bis(4-nitrophenyl)perhydrofuro-[2,3-b]furan-3-yl]triisopropylsilane
    Light, ME
    Hursthouse, MB
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2002, 58 : o252 - o253
  • [27] (2S,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)proline]
    Best, Daniel
    Jenkinson, Sarah F.
    Thompson, Amber L.
    Watkin, David J.
    Wilson, Francis X.
    Nash, Robert J.
    Fleet, George W. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2418 - +
  • [28] Efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde
    Canoy, Will L.
    Cooley, Bob E.
    Corona, John A.
    Lovelace, Thomas C.
    Millar, Alan
    Weber, Aimee M.
    Xie, Shiping
    Zhang, Yong
    ORGANIC LETTERS, 2008, 10 (06) : 1103 - 1106
  • [29] STRUCTURE OF (2R,4R,5R)-2-CHLORO-3-ISOPROPYL-4-METHYL-5-PHENYL-1,3,2-OXAZAPHOSPHOLIDINE 2-OXIDE
    ROBINSON, PD
    HUA, DH
    ROCHE, D
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 923 - 925
  • [30] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
    BASHYAL, BP
    CHOW, HF
    FELLOWS, LE
    FLEET, GWJ
    TETRAHEDRON, 1987, 43 (02) : 415 - 422