Stereoselective synthesis of (-)-microcarpalide

被引：27
作者：
Chavan, SP [1 ]
Praveen, C [1 ]
机构：
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 11期
关键词：
microcarpalide; ring-closing metathesis; sharpless asymmetric dihydroxylation; Claisen ortho ester rearrangement; cis-2-butene-1,4-diol;
D O I：
10.1016/j.tetlet.2005.01.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly convergent and efficient synthesis of (-)-microcarpalide, a 10-membered lactone displaying remarkable microfilament disrupting activity is described. Ring-closing metathesis and Sharpless asymmetric dihydroxylations are the key steps. Our strategy highlights the application of novel hydroxy lactone precursors for the stereoselective synthesis of (-)-microcarpalide. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1939 / 1941
页数：3
相关论文
共 17 条
  • [1] Banwell MG, 2004, HETEROCYCLES, V62, P713
  • [2] Enantioselective synthesis of R-(+)-α and S-(-)-α-lipoic acid
    Chavan, SP
    Praveen, C
    Ramakrishna, G
    Kalkote, UR
    [J]. TETRAHEDRON LETTERS, 2004, 45 (31) : 6027 - 6028
  • [3] A concise and stereoselective synthesis of (+)- and (-)-deoxoprosophylline
    Chavan, SP
    Praveen, C
    [J]. TETRAHEDRON LETTERS, 2004, 45 (02) : 421 - 423
  • [4] Structure elucidation and synthesis of (4S,5S,6Z,8E)-5-hydroxydeca-6,8-dien-4-olide [(S,S)-sapinofuranone B] -: a novel γ-lactone metabolite of Acremonium strictum
    Clough, S
    Raggatt, ME
    Simpson, TJ
    Willis, CL
    Whiting, A
    Wrigley, SK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2475 - 2481
  • [5] Total synthesis of (-)-microcarpalide, a novel microfilament disrupting metabolite
    Davoli, P
    Spaggiari, A
    Castagnetti, L
    Prati, F
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (01) : 38 - 47
  • [6] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
  • [7] Recent advances in olefin metathesis and its application in organic synthesis
    Grubbs, RH
    Chang, S
    [J]. TETRAHEDRON, 1998, 54 (18) : 4413 - 4450
  • [8] Total synthesis of microcarpalide
    Gurjar, MK
    Nagaprasad, R
    Ramana, CV
    [J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2873 - 2875
  • [9] HANACK M, 1978, SYNTHESIS-STUTTGART, P26
  • [10] TOTAL SYNTHESIS OF (+)-NOJIRIMYCIN AND (+)-1-DEOXYNOJIRIMYCIN
    IIDA, H
    YAMAZAKI, N
    KIBAYASHI, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) : 3337 - 3342
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