A two-step biomimetic synthesis of antimalarial robustadials A and B

被引：32
作者：
Bharate, Sandip B. [1 ]
Singh, Inder Pal [1 ]
机构：
[1] NIPER, Dept Nat Prod, SAS Nagar 160062, Punjab, India
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 39期
关键词：
robustadials A and B; antimalarial; phloroglucinol; biomimetic synthesis;
D O I：
10.1016/j.tetlet.2006.07.113
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The antimalarial robustadials A and B have been synthesized in two steps starting from commercially available phloroglucinol comprising a key biomimetic three-component reaction that involves in situ generation of an o-quinone methide via Knoevenagel condensation and subsequent Diels-Alder cycloaddition with (-)-beta-pinene. @ 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7021 / 7024
页数：4
相关论文
共 19 条
  • [1] ARISAWA M, 1990, CHEM PHARM BULL, V38, P1624, DOI 10.1248/cpb.38.1624
  • [2] The synthesis of (-)-robustadial A and some analogues
    Aukrust, IR
    Skattebol, L
    [J]. ACTA CHEMICA SCANDINAVICA, 1996, 50 (02): : 132 - 140
  • [3] Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
    Bharate, SB
    Bhutani, KK
    Khan, SI
    Tekwani, BL
    Jacob, MR
    Khan, IA
    Singh, IP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (06) : 1750 - 1760
  • [4] An efficient two-step synthesis of jensenone isolated from Eucalyptus jensenii.: Synthesis of analogues and evaluation as antioxidants
    Bharate, SB
    Chauthe, SK
    Bhutani, KK
    Singh, IP
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (07) : 551 - 555
  • [5] REVISED STRUCTURES OF ROBUSTADIALS A AND B FROM EUCALYPTUS-ROBUSTA
    CHENG, Q
    SNYDER, JK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4562 - 4567
  • [6] Electrochemical synthesis of euglobal-G1, -G2, -G3, -G4, -T1 and -IIc
    Chiba, K
    Arakawa, T
    Tada, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2939 - 2942
  • [7] Synthesis of euglobal-G3 and -G4
    Chiba, K
    Arakawa, T
    Tada, M
    [J]. CHEMICAL COMMUNICATIONS, 1996, (15) : 1763 - 1764
  • [8] Bioactive acylphloroglucinol derivatives from Eucalyptus species
    Ghisalberti, EL
    [J]. PHYTOCHEMISTRY, 1996, 41 (01) : 7 - 22
  • [9] Phloroglucin dialdehydes and its homologues.
    Gruber, W
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1942, 75 : 29 - 33
  • [10] STEREOSELECTIVE SYNTHESIS OF PRECURSORS OF NATURALLY-OCCURRING ROBUSTADIALS-A AND ROBUSTADIALS-B
    KOSER, S
    HOFFMANN, HMR
    WILLIAMS, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6163 - 6165
12