Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans

被引:71
|
作者
Al-Mutairi, EH
Crosby, SR
Darzi, J
Harding, JR
Hughes, RA
King, CD
Simpson, TJ
Smith, RW
Willis, CL
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England
关键词
D O I
10.1039/b101414p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclisation of homoallylic acetals under acidic conditions leads to the formation of 2,4,5-trisubstituted tetrahydropyrans with the creation of two new asymmetric centres with excellent stereocontrol. By varying the acid and the nucleophile, the reaction may be adapted for the preparation of 2,4,5-trisubstituted tetrahydropyrans with either a halide, alcohol, acetate or amide at C-4.
引用
收藏
页码:835 / 836
页数:2
相关论文
共 50 条
  • [1] Stereoselective synthesis of 2,4,5-trisubstituted tetrahydropyrans using an intramolecular allylation strategy
    Jervis, Peter J.
    Kariuki, Benson M.
    Cox, Liam R.
    ORGANIC LETTERS, 2006, 8 (20) : 4648 - +
  • [2] Synthesis of 2,4,5-trisubstituted tetrahydropyrans as peptidomimetic scaffolds for melanocortin receptor ligands
    Kulesza, A
    Ebetino, FH
    Mishra, RK
    Cross-Doersen, D
    Mazur, AW
    ORGANIC LETTERS, 2003, 5 (08) : 1163 - 1166
  • [3] SYNTHESIS OF 2,4,5-TRISUBSTITUTED PYRIMIDINES
    Pawar, M. J.
    Burungale, A. S.
    Karale, B. K.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 20 (02) : 133 - 136
  • [4] Synthesis of 2,4,5-trisubstituted oxazoles
    Cai, XH
    Yang, HJ
    Zhang, GL
    SYNTHESIS-STUTTGART, 2005, (10): : 1569 - 1571
  • [5] Stereocontrolled synthesis of trisubstituted tetrahydropyrans
    Cloninger, MJ
    Overman, LE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) : 1092 - 1093
  • [6] A CONVENIENT SYNTHESIS OF 2,4,5-TRISUBSTITUTED OXAZOLES
    REDDY, GS
    BHATT, MV
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (04): : 322 - 323
  • [7] THE SYNTHESIS OF SOME 2,4,5-TRISUBSTITUTED PYRIMIDINES
    PETERS, E
    MINNEMEYER, HJ
    SPEARS, AW
    TIECKELMANN, H
    JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (12): : 2137 - 2142
  • [8] Stereocontrolled synthesis of trisubstituted tetrahydropyrans.
    Cloninger, MJ
    Overman, LE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U169 - U169
  • [9] Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans
    Cooper, Dennis A.
    Robbins, Emma
    Tizzard, Graham J.
    Coles, Simon J.
    O'Brien, Matthew
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3441 - 3455
  • [10] Asymmetric Synthesis of 2,4,5-Trisubstituted 2-Thiazolines
    Bengtsson, Christoffer
    Nelander, Hanna
    Almqvist, Fredrik
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (30) : 9916 - 9922