A total synthesis of spiruchostatin A

被引：56
作者：
Doi, T
Iijima, Y
Kazuo, SY
Ganesan, A
Takahashi, T
机构：
[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
[2] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan
[3] Natl Inst Adv Ind Sci & Technol, BIRC, Prot Network Team, Low MW Chem Lab,Kota Ku, Tokyo 1350064, Japan
[4] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 07期
关键词：
spiruchostatin; cyclic depsipeptide; natural product synthesis; asymmetric aldol reaction;
D O I：
10.1016/j.tetlet.2005.12.031
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization Using the Shiina method. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码：1177 / 1180
页数：4
相关论文
共 29 条
  • [11] 2-X
  • [12] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION
    INANAGA, J
    HIRATA, K
    SAEKI, H
    KATSUKI, T
    YAMAGUCHI, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 1989 - 1993
  • [13] Synthesis of the C-1027 chromophore framework through atropselective macrolactonization
    Inoue, M
    Sasaki, T
    Hatano, S
    Hirama, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) : 6500 - 6505
  • [14] ISOBE T, 1995, Patent No. 09143173
  • [15] SYNTHESIS OF THE CYCLODEPSIPEPTIDE NORDIDEMNIN-B, A CYTO-TOXIC MINOR PRODUCT ISOLATED FROM THE SEA TUNICATE TRIDIDEMNUM-CYANOPHORUM
    JOUIN, P
    PONCET, J
    DUFOUR, MN
    PANTALONI, A
    CASTRO, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) : 617 - 627
  • [16] THE SYNTHESIS OF CYSTINE PEPTIDES BY IODINE OXIDATION OF S-TRITYL-CYSTEINE AND S-ACETAMIDOMETHYL-CYSTEINE PEPTIDES
    KAMBER, B
    HARTMANN, A
    EISLER, K
    RINIKER, B
    RINK, H
    SIEBER, P
    RITTEL, W
    [J]. HELVETICA CHIMICA ACTA, 1980, 63 (04) : 899 - 915
  • [17] ASYMMETRIC ALDOL REACTION OF AMIDE ENOLATES BEARING TRANS-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES
    KATSUKI, T
    YAMAGUCHI, M
    [J]. TETRAHEDRON LETTERS, 1985, 26 (47) : 5807 - 5810
  • [18] Total synthesis of the antitumor depsipeptide FR-901,228
    Li, KW
    Wu, J
    Xing, WN
    Simon, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) : 7237 - 7238
  • [19] Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp.
    Masuoka, Y
    Nagai, A
    Shin-ya, K
    Furihata, K
    Nagai, K
    Suzuki, K
    Hayakawa, Y
    Seto, H
    [J]. TETRAHEDRON LETTERS, 2001, 42 (01) : 41 - 44
  • [20] MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS
    MOHAMADI, F
    RICHARDS, NGJ
    GUIDA, WC
    LISKAMP, R
    LIPTON, M
    CAUFIELD, C
    CHANG, G
    HENDRICKSON, T
    STILL, WC
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) : 440 - 467
123