Synthesis of spiroketal fragment of ossamycin via Prins cyclization

被引：7
|
作者：
Yadav, J. S. [1 ]
Rahman, Md. Ataur [1 ]
Reddy, N. Mallikarjuna [1 ]
Prasad, A. R. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Ctr Semiochem, Acad Sci & Innovat Res AcSIR, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 02期
关键词：
Natural products; Antitumour antibiotic; Prins cyclization; Reductive opening; Spiroketals; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; REDUCTIVE CLEAVAGE; CYTOVARICIN; OLIGOMYCIN; SEGMENT;
D O I：
10.1016/j.tetlet.2014.11.097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric synthesis of spiroketal fragment of an antitumour antibiotic, ossamycin is described. Coupling of aldehyde and alkyne fragments followed by spiroketalization has afforded the spiroketal sub unit of ossamycin. Both the sub targets were constructed via Prins cyclization. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：365 / 367
页数：3
相关论文
共 50 条
  • [31] Total synthesis of diospongin A via an enzymatic kinetic resolution of (±)-tetrahydropyranol derived from Prins cyclization
    Yadav, J. S.
    Padmavani, B.
    Reddy, B. V. Subba
    Venugopal, Ch.
    Rao, A. Bhaskar
    SYNLETT, 2007, (13) : 2045 - 2048
  • [32] Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization
    Luo, Hai-Qing
    Hu, Xu-Hong
    Loh, Teck-Peng
    TETRAHEDRON LETTERS, 2010, 51 (07) : 1041 - 1043
  • [33] Application of Prins cyclization to the total synthesis of (+)-decytospolides A and B
    Clarisse, Damien
    Fache, Fabienne
    TETRAHEDRON LETTERS, 2014, 55 (14) : 2221 - 2222
  • [34] Synthesis of 4-iodotetrahydropyran-containing polymers via TMSI-promoted Prins cyclization
    Inagi, Shinsuke
    Takei, Naoko
    Fuchigami, Toshio
    POLYMER CHEMISTRY, 2013, 4 (04) : 1221 - 1227
  • [35] An efficient approach to the synthesis of 3-vinylidene tetrahydropyrans via Prins-type cyclization
    Dziedzic, M
    Lipner, G
    Furman, B
    TETRAHEDRON LETTERS, 2005, 46 (40) : 6861 - 6863
  • [36] Micro and mesoporous materials based on zeolite Y for the florol synthesis via the prins cyclization of isoprenol
    Demuth, Pascal
    Gallego-Villada, Luis A.
    Maki-Arvela, Paivi
    Majidov, Ramin
    Vajglova, Zuzana
    Kumar, Narendra
    Angervo, Ilari
    Lastusaari, Mika
    Eranen, Kari
    Murzin, Dmitry Yu.
    CATALYSIS TODAY, 2024, 433
  • [37] Synthesis of catechin analogs via indium chloride mediated Prins-type cyclization.
    Li, CJ
    Li, JK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U120 - U120
  • [38] Formal synthesis of (+)-SCH 351448: the Prins cyclization approach
    Chan, Kok-Ping
    Ling, Yvonne Hui
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2007, (09) : 939 - 941
  • [39] Heteropoly acid catalysts in Prins cyclization for the synthesis of Florol?
    de Meireles, Augusto L. P.
    da Silva Rocha, Kelly A.
    Kozhevnikova, Elena F.
    Kozhevnikov, Ivan V.
    Gusevskaya, Elena V.
    MOLECULAR CATALYSIS, 2021, 502
  • [40] Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines
    Amemiya, Sho
    Okemoto, Shingo
    Tsubouchi, Akira
    Saito, Akio
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (13) : 2959 - 2967
12345