A modular total synthesis of aculeatins A, B, E, F and 6-epi-aculeatins E, F

被引：15
|
作者：
Ramana, C. V. [1 ]
Pandey, Sunil Kumar [1 ]
机构：
[1] Natl Chem Lab, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON | 2010年 / 66卷 / 01期
关键词：
Natural products synthesis; Aculeatins; Alkyne-oxirane coupling; Oxidative spiroketalization; Sonogashira coupling; DIVERSITY-ORIENTED SYNTHESIS; CARBOHYDRATE-BASED APPROACH; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE HYDROGENOLYSIS; ABSOLUTE-CONFIGURATIONS; MPM; 4-METHOXYBENZYL; FOCUSED LIBRARY; BENZYL; SONOGASHIRA; DERIVATIVES;
D O I：
10.1016/j.tet.2009.10.058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of aculeatins A, B. E and F confirming the assigned absolute configuration of recently isolated aculeatins E and F is documented. A convergent approach has been designed by the addition of both the terminal units (phenol and side chain) at an advanced stage. The central 1,3,5-triol unit with the requisite stereochemistry was prepared from the commercially available alpha-D-glucoheptonic-gamma-lactone. Selective O-debenzylation during the hydrogenolysis of the diyne intermediate and the one pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total syntheses. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：390 / 399
页数：10
相关论文
共 50 条
  • [31] Total synthesis and biological evaluation of oscillatoxins D, E, and F
    Araki, Yusuke
    Hanaki, Yusuke
    Kita, Masaki
    Hayakawa, Koutaro
    Irie, Kazuhiro
    Nokura, Yoshihiko
    Nakazaki, Atsuo
    Nishikawa, Toshio
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2021, 85 (06) : 1371 - 1382
  • [32] Total synthesis of two neolignans for (±)-Eusiderin E and (±)-Eusiderin F
    Jing, XB
    Gu, WX
    Bie, PY
    Ren, XF
    Pan, XF
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2001, 22 (01): : 63 - 66
  • [33] Enantioselective total synthesis and stereochemical revision of communiols E and F
    Enomoto, Masaru
    Kuwahara, Shigefumi
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16): : 6287 - 6290
  • [34] B=F(P,E)
    STERN, GG
    JOURNAL OF PROJECTIVE TECHNIQUES & PERSONALITY ASSESSMENT, 1964, 28 (02): : 161 - 168
  • [35] Total Syntheses of Kapakahines E and F
    Rainier, Jon D.
    Espejo, Vinson R.
    ISRAEL JOURNAL OF CHEMISTRY, 2011, 51 (3-4) : 473 - 482
  • [36] E2f3a and E2f3b make overlapping but different contributions to total E2f3 activity
    Danielian, P. S.
    Friesenhahn, L. B.
    Faust, A. M.
    West, J. C.
    Caron, A. M.
    Bronson, R. T.
    Lees, J. A.
    ONCOGENE, 2008, 27 (51) : 6561 - 6570
  • [37] E2f3a and E2f3b make overlapping but different contributions to total E2f3 activity
    P S Danielian
    L B Friesenhahn
    A M Faust
    J C West
    A M Caron
    R T Bronson
    J A Lees
    Oncogene, 2008, 27 : 6561 - 6570
  • [38] Total Synthesis of 4-epi-Bengamide E
    Forconesi, Gabriella Vitali
    Basso, Andrea
    Banfi, Luca
    Gugliotta, Davide
    Lambruschini, Chiara
    Nola, Marta
    Riva, Renata
    Rocca, Valeria
    Moni, Lisa
    MOLECULES, 2024, 29 (08):
  • [39] Asymmetric total synthesis of 5′-epi-paecilomycin-F
    Jana, Nandan
    Nanda, Samik
    TETRAHEDRON-ASYMMETRY, 2012, 23 (10) : 802 - 808
  • [40] Total synthesis of motualevic acids A-F, (E) and (Z)-antazirines
    Kadam, Vilas D.
    Sudhakar, Gangarajula
    TETRAHEDRON, 2015, 71 (07) : 1058 - 1067
12345