Stereoselective Total Synthesis of Paecilomycins E and F

被引:16
作者
Bhunia, Nisith [1 ]
Das, Biswanath [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 10期
关键词
resorcylic acid lactones; paecilomycin E; paecilomycin F; total synthesis; cis-butene-1; 4-diol; RESORCYLIC ACID LACTONES; ASYMMETRIC TOTAL-SYNTHESIS; AIGIALOMYCIN-D; GIBBERELLA-ZEAE; NATURAL-PRODUCTS; APICULAREN-A; FUNGUS; HSP90; INHIBITION; MACROLIDES;
D O I
10.1055/s-0034-1380400
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective total synthesis of two bioactive resorcylic acid lactones, paecilomycins E and F has been accomplished thorough a general pathway using cis-butene-1,4-diol as the starting material. The pivotal steps of the synthesis include Sharpless asymmetric epoxidation, Bestmann-Ohira alkynation, Jacobsen kinetic resolution, and Heck coupling reaction.
引用
收藏
页码:1499 / 1509
页数:11
相关论文
共 64 条
  • [51] Pochonins K-P: new radicicol analogues from Pochonia chlamydosporia var. chlamydosporia and their WNT-5A expression inhibitory activities
    Shinonaga, Hideki
    Kawamura, Yoji
    Ikeda, Akiko
    Aoki, Mari
    Sakai, Noriyoshi
    Fujimoto, Natsuko
    Kawashima, Akira
    [J]. TETRAHEDRON, 2009, 65 (17) : 3446 - 3453
  • [52] Stereoselective total synthesls of paecilomycin E
    Srihari, P.
    Mahankali, B.
    Rajendraprasad, K.
    [J]. TETRAHEDRON LETTERS, 2012, 53 (01) : 56 - 58
  • [53] ISOLATION OF AN ANABOLIC, UTEROTROPHIC COMPOUND FROM CORN INFECTED WITH GIBBERELLA ZEAE
    STOB, M
    BALDWIN, RS
    GILLETTE, KG
    ANDREWS, FN
    TUITE, J
    [J]. NATURE, 1962, 196 (4861) : 1318 - +
  • [54] Sudhakar C, 2012, EUR J ORG CHEM, V2012, P1253, DOI 10.1002/ejoc.201101601
  • [55] Three-component coupling approach toward the synthesis of a resorcylic acid lactone framework
    Sugiyama, Sakae
    Fuse, Shinichiro
    Takahashi, Takashi
    [J]. TETRAHEDRON, 2011, 67 (35) : 6654 - 6658
  • [56] SYNTHESIS OF (+/-)-DIMETHYL CURVULARIN BASED ON THE PALLADIUM-CATALYZED CARBONYLATION OF 3,5-DIMETHOXYBENZYL CHLORIDE USING A BUTADIENE TELOMER AS A BUILDING BLOCK
    TAKAHASHI, T
    IKEDA, H
    TSUJI, J
    [J]. TETRAHEDRON LETTERS, 1980, 21 (40) : 3885 - 3888
  • [57] WANG Z, 1985, TETRAHEDRON LETT, V26, P6221
  • [58] Chemistry and biology of resorcylic acid lactones
    Winssinger, Nicolas
    Barluenga, Sofia
    [J]. CHEMICAL COMMUNICATIONS, 2007, (01) : 22 - 36
  • [59] Hsp90 Inhibition with Resorcylic Acid Lactones (RALs)
    Winssinger, Nicolas
    Fontaine, Jean-Gonzague
    Barluenga, Sofia
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2009, 9 (15) : 1419 - 1435
  • [60] β-Resorcylic Acid Lactones from a Paecilomyces Fungus (vol 73, pg 885, 2010)
    Xu, Liangxiong
    He, Zhengxiang
    Xue, Jinghua
    Chen, Xiaoping
    Wei, Xiaoyi
    [J]. JOURNAL OF NATURAL PRODUCTS, 2012, 75 (05): : 1006 - 1006