Enantio- and diastereoselective synthesis of (-)-semburin and (-)-isosemburin, monoterpenes isolated from Swertia japonica

被引：0
|
作者：
Kadota, K [1 ]
Taniguchi, T [1 ]
Ogasawara, K [1 ]
机构：
[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan
来源：
SYNLETT | 2002年 / 02期
关键词：
chiral building block; intramolecular ene reaction; monoterpene; 7,8-dioxabicyclo[3.2.1]octane framework; 2,8-dioxabicyclo[3.3.1]nonane framework;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantio- and diastereocontrolled synthesis of two monoterpenes having a 2,8-dioxabicyclo[3.3.1]nonane framework, (-)-semburin and (-)-isosemburin, isolated from Swertia japonica, has been developed starting from the chiral building block having a 7,8-dioxabicyclo[3.2.1]octane framework.
引用
收藏
页码：334 / 336
页数：3
相关论文
共 50 条
  • [1] THE STRUCTURES OF SEMBURIN AND ISOSEMBURIN, 2,8-DIOXABICYCLO[3.3.1] NONANES ISOLATED FROM THE VOLATILE OIL OF SWERTIA-JAPONICA MAKINO
    SAKAI, T
    NAOKI, H
    TAKAKI, K
    KAMEOKA, H
    [J]. CHEMISTRY LETTERS, 1981, (09) : 1257 - 1258
  • [2] Enantio- and diastereoselective synthesis of erysulfone and erysulfoxide
    Bourdeau, L
    Sutherland, AG
    [J]. TETRAHEDRON LETTERS, 1997, 38 (52) : 9081 - 9084
  • [3] Enantio- and diastereoselective synthesis of γ-amino alcohols
    Verkade, Jorge M. M.
    Quaedflieg, Peter J. L. M.
    Verzijl, Gerard K. M.
    Lefort, Laurent
    van Delft, Floris L.
    de Vries, Johannes G.
    Rutjes, Floris P. J. T.
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (77) : 14462 - 14464
  • [4] Enantio- and diastereoselective synthesis of (R,R)-β-Methoxytyrosine
    Cranfill, David C.
    Lipton, Mark A.
    [J]. ORGANIC LETTERS, 2007, 9 (18) : 3511 - 3513
  • [5] Enantio- and Diastereoselective Synthesis of Spiro-epoxyoxindoles
    Boucherif, Amina
    Yang, Qing-Qing
    Wang, Qiang
    Chen, Jia-Rong
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 3924 - 3929
  • [6] Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst
    Kawauchi, Genki
    Umemiya, Shigenobu
    Taniguchi, Tohru
    Monde, Kenji
    Hayashi, Yujiro
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (33) : 8409 - 8414
  • [7] An enantio- and diastereoselective synthesis of (-)-isoretronecanol and (+)-trachelanthamidine from a meso precursor
    Konno, H
    Kishi, M
    Hiroya, K
    Ogasawara, K
    [J]. HETEROCYCLES, 1998, 49 : 33 - 37
  • [8] Enantio- and diastereoselective synthesis of β-substituted-δ-aminoboronic esters from nitriles
    Ramachandran, P. Veeraraghavan
    Mitsuhashi, Wataru
    Biswas, Debanjan
    Nicponski, Daniel R.
    [J]. TETRAHEDRON LETTERS, 2013, 54 (36) : 4830 - 4833
  • [9] Enantio- and diastereoselective synthesis of 4′-α-substituted carbocyclic nucleosides
    Kato, K
    Suzuki, H
    Tanaka, H
    Miyasaka, T
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (06) : 911 - 914
  • [10] Enantio- and Diastereoselective Synthesis of β,γ,γ,δ-Tetrasubstituted α-Methylene-δ-lactones
    Albrecht, Lukasz
    Deredas, Dariusz
    Wojciechowski, Jakub
    Wolf, Wojciech M.
    Krawczyk, Henryk
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (02): : 247 - 252
12345