Asymmetric total synthesis of 5′-epi-paecilomycin-F

被引:25
|
作者
Jana, Nandan [1 ]
Nanda, Samik [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
RESORCYLIC ACID LACTONES; DYNAMIC KINETIC RESOLUTION; KINASE INHIBITOR; AIGIALOMYCIN-D; ESTROGENIC ACTIVITY; RUTHENIUM; RADICICOL; LL-Z1640-2; ALCOHOLS; MACROLIDES;
D O I
10.1016/j.tetasy.2012.05.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric total synthesis of one of the stereoisomers of the naturally occurring 14-membered ring macrolide paecilomycin-F (5'-epi) has been reported in this article. The main highlight of the synthetic strategy involves the successful application of a ring closing metathesis (RCM) reaction at a late stage. Asymmetric Keck allylation, Sharpless asymmetric dihydroxylation, and Mitsunobu esterification have also been used successfully for the total synthesis of 5'-epi-paecilomycin-F. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:802 / 808
页数:7
相关论文
共 50 条
  • [1] Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C
    Pal, Pratik
    Jana, Nandan
    Nanda, Samik
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (41) : 8257 - 8274
  • [2] A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′-epi-Cochliomycin C
    Mahankali, Bakkolla
    Srihari, Pabbaraja
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (18) : 3983 - 3993
  • [3] Asymmetric total synthesis of 5′-epi-cochliomycin C
    Jana, Nandan
    Das, Debabrata
    Nanda, Samik
    TETRAHEDRON, 2013, 69 (14) : 2900 - 2908
  • [4] Total Synthesis of Paecilomycin B
    Ohba, Kiyomi
    Nakata, Masaya
    ORGANIC LETTERS, 2015, 17 (12) : 2890 - 2893
  • [5] Stereoselective total synthesis of paecilomycin E and F and its two congeners Cochliomycin C and 6-epi-Cochliomycin C
    Kadari, Sudhakar
    Yerrabelly, Hemasri
    Yerrabelly, Jayaprakash Rao
    Gogula, Thirupathi
    Goud, Yadaiah
    Thalari, Gangadhar
    Doda, Sai Reddy
    SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1867 - 1875
  • [6] Stereoselective total synthesis of antiplasmodial resorcylic acid lactone paecilomycin F
    Bakkolla, Mahankali
    Pabbaraja, Srihari
    ARKIVOC, 2016, : 123 - 136
  • [7] Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide
    Chakraborty, Joy
    Nanda, Samik
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (31) : 7369 - 7379
  • [8] Convergent Total Synthesis of Paecilomycin B and 6′-epi-Paecilomycin B by a Barbier-Type Reaction Using 2,4,6-Triisopropylphenyllithium
    Ohba, Kiyomi
    Nakata, Masaya
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (13): : 7019 - 7032
  • [9] Asymmetric total synthesis of (+)-2-epi-deoxoprosopinine
    Enders, D
    Kirchhoff, JH
    SYNTHESIS-STUTTGART, 2000, (14): : 2099 - 2105
  • [10] A Concise and Stereoselective Total Synthesis of Paecilomycin E
    Reddy, A. Srinivas
    Bhavani, Gundamalla
    Jonnala, Sandhya
    Bantu, Rajashaker
    Reddy, B. V. Subba
    NATURAL PRODUCT COMMUNICATIONS, 2019, 14 (01) : 131 - 133