Stereoselective Total Synthesis of Decytospolides A and B Starting from D-Mannitol

被引:4
|
作者
Srilatha, Malampati [1 ]
Das, Biswanath [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1002/hlca.201400200
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereoselective total synthesis of decytospolides A and B, two naturally occurring pyran derivatives, has been achieved using D-mannitol as the starting material. The intramolecular oxa-Michael reaction has been employed to construct the tetrahydropyran ring of the molecules and Weinreb amide formation to generate their side chain with a keto function.
引用
收藏
页码:267 / 272
页数:6
相关论文
共 50 条
  • [31] Novel monodentate phosphoramidites by chiral pool synthesis starting from D-mannitol, and their PdII and RhI complexes
    Bayer, A
    Thewalt, U
    Rieger, B
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2002, (01) : 199 - 203
  • [32] Efficient Asymmetric Synthesis of Oseltamivir from D-Mannitol
    Mandai, Tadakatsu
    Oshitari, Tetsuta
    SYNLETT, 2009, (05) : 783 - 786
  • [33] Synthesis of a small library of mixed-acid phospholipids from D-Mannitol as a homochiral starting material
    Xia, J
    Hui, YZ
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (11) : 1659 - 1663
  • [34] THIOSUGARS FROM D-MANNITOL
    FUZIER, M
    LEMERRER, Y
    DEPEZAY, JC
    TETRAHEDRON LETTERS, 1995, 36 (36) : 6443 - 6446
  • [35] SYNTHESIS OF ENANTIOMERICALLY PURE (S)-1,2-EPOXY-4-METHYLPENTANE STARTING FROM D-MANNITOL
    ROSSI, R
    CARPITA, A
    BONACCORSI, F
    CHIMICA & L INDUSTRIA, 1983, 65 (11): : 694 - 695
  • [36] Synthesis of enantiopure polyhydroxylated carbo and sulfurated cycles with potential or proved biological activity, starting from D-mannitol
    Cerè, V
    Peri, F
    Pollicino, S
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 153 : 305 - 306
  • [37] Enantiodivergent synthesis of both enantiomeric forms of substituted paraconic acids starting from D-mannitol as a chiral pool
    Masaki, Y
    Arasaki, H
    Itoh, A
    TETRAHEDRON LETTERS, 1999, 40 (26) : 4829 - 4832
  • [38] Microwave assisted enantiospecific synthesis of γ-hydroxythreonine from D-mannitol
    Bose, AK
    Banik, BK
    Bhattacharjee, A
    Manhas, MS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U238 - U238
  • [39] Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose
    Chida, N
    Sugihara, K
    Amano, S
    Ogawa, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (03): : 275 - 280
  • [40] An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: total synthesis of (-)-muricatacin
    Chandrasekhar, M
    Chandra, KL
    Singh, VK
    TETRAHEDRON LETTERS, 2002, 43 (15) : 2773 - 2775