Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors

被引:8
|
作者
Gadikota, RR [1 ]
Keller, AI [1 ]
Callam, CS [1 ]
Lowary, TL [1 ]
机构
[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA
关键词
D O I
10.1016/S0957-4166(03)00078-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:737 / 742
页数:6
相关论文
共 50 条
  • [31] An efficient synthesis of orthogonally protected trans- and cis-4-aminopipecolic acid
    Szatmari, Istvan
    Kiss, Lorand
    Fueloep, Ferenc
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) : 1387 - 1389
  • [32] An efficient and highly stereoselective synthesis of β,γ-trans-β-benzoyl-γ-aryl-γ-butyrolactones
    Cao, WG
    Ding, WY
    Chen, YL
    Qiu, MY
    SYNTHETIC COMMUNICATIONS, 2000, 30 (20) : 3793 - 3799
  • [33] Correlation of the Rates of Solvolysis of Two Arenesulfonyl Chlorides and of trans-β-Styrenesulfonyl Chloride - Precursors in the Development of New Pharmaceuticals
    Ryu, Zoon Ha
    Lee, Sang Wok
    D'Souza, Malcolm J.
    Yaakoubd, Lamia
    Feld, Samantha E.
    Kevill, Dennis N.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2008, 9 (12) : 2639 - 2657
  • [34] From TER to trans- and paracellular resistance: lessons from impedance spectroscopy
    Guenzel, Dorothee
    Zakrzewski, Silke S.
    Schmid, Thomas
    Pangalos, Maria
    Wiedenhoeft, John
    Blasse, Corinna
    Ozboda, Christopher
    Krug, Susanne M.
    BARRIERS AND CHANNELS FORMED BY TIGHT JUNCTION PROTEINS I, 2012, 1257 : 142 - 151
  • [35] Syntheses of Complex Terpenes from Simple Polyprenyl Precursors
    Magnani, Claire S. Harmange
    Thach, Danny Q.
    Haelsig, Karl T.
    Maimone, Thomas J.
    ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) : 949 - 961
  • [36] VERSATILE SYNTHESES OF CHIRAL CARBOCYCLES FROM SUGAR PRECURSORS
    HORTON, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 2 - CARB
  • [37] The total synthesis of macrosphelides A and E from carbohydrate precursors
    Sharma, GVM
    Mouli, CC
    TETRAHEDRON LETTERS, 2002, 43 (50) : 9159 - 9161
  • [38] THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES FROM ACYCLIC PRECURSORS
    AGER, DJ
    EAST, MB
    TETRAHEDRON, 1993, 49 (26) : 5683 - 5765
  • [39] Highly efficient chemoenzymatic syntheses of trans-2-aminocyclopentanol derivatives
    Gonzalez-Sabin, Javier
    Moris-Varas, Francisco
    Pena, Carmen
    Rebolledo, Francisca
    Gotor, Vicente
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2009, 59 (1-3) : 111 - 115
  • [40] An efficient synthesis of trans-γ-oxo-α,β-unsaturated carboxylic acids, the intermediates for patulolide A and pyrenophorin
    Davis, KJ
    Bhalerao, UT
    Rao, BV
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2001, 40 (08): : 656 - 661