Total synthesis of (±) Xyloketal H

被引:5
|
作者
Bhosale, Viraj A. [1 ]
Kulkarni, Mukund G. [1 ]
机构
[1] Savitribai Phule Pune Univ, Dept Chem, Pune 411007, Maharashtra, India
关键词
Claisen rearrangement; Grignard; Oxidation; Ozonolysis; Wittig olefination; FUNGUS XYLARIA SP; METHIDE INTERMEDIATE GENERATION; NATURAL-PRODUCTS; BIOMIMETIC SYNTHESIS; EFFICIENT METHOD; METABOLITE; CORE;
D O I
10.1016/j.tetlet.2015.03.118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient total synthesis of (+/-) Xyloketal H is described, the Wittig olefination-Claisen rearrangement protocol has served here as the key transformation for constructing the core structure of the metabolite. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2568 / 2570
页数:3
相关论文
共 50 条
  • [1] Total synthesis of (-)-xyloketal A
    Pettigrew, JD
    Wilson, PD
    ORGANIC LETTERS, 2006, 8 (07) : 1427 - 1429
  • [2] Total synthesis of (±)-xyloketal D and model studies towards the total synthesis of (-)-xyloketal A
    Pettigrew, JD
    Bexrud, JA
    Freeman, RP
    Wilson, PD
    HETEROCYCLES, 2004, 62 : 445 - 452
  • [3] Total synthesis of (-)-xyloketal D and its enantiomer - Confirmation of absolute stereochemistry
    Pettigrew, JD
    Freeman, RP
    Wilson, PD
    CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (11) : 1640 - 1648
  • [4] Chemoenzymatic Synthesis of (+)-Xyloketal B
    Romero, Evan O.
    Perkins, Jonathan C.
    Burch, Jessica E.
    Delgadillo, David A.
    Nelson, Hosea M.
    Narayan, Alison R. H.
    ORGANIC LETTERS, 2023, : 1547 - 1552
  • [5] CONCISE SYNTHESIS OF XYLOKETAL C ANALOGUES
    Huang, Yan
    Lin, Yong-Cheng
    HETEROCYCLES, 2009, 78 (03) : 749 - 755
  • [6] Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus Xylaria sp.
    Krohn, K
    Riaz, M
    TETRAHEDRON LETTERS, 2004, 45 (02) : 293 - 294
  • [7] Synthesis of xyloketal A, B, C, D, and G analogues
    Pettigrew, JD
    Wilson, PD
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04): : 1620 - 1625
  • [8] Xyloketal H from the mangrove endophytic fungus Xylaria sp 2508
    Liu, X.
    Xu, F.
    Zhang, Y.
    Liu, L.
    Huang, H.
    Cai, X.
    Lin, Y.
    Chan, W.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (06) : 1091 - 1092
  • [9] Total Synthesis of Gabosine H
    Prasad, Kavirayani R.
    Kumar, S. Mothish
    SYNLETT, 2011, (11) : 1602 - 1604
  • [10] Total synthesis of largamide H
    Liang, Shuo
    Xu, Zhengshuang
    Ye, Tao
    CHEMICAL COMMUNICATIONS, 2010, 46 (01) : 153 - 155