An enantioselective total synthesis of Sch-725674

被引：23
|
作者：
Ramakrishna, Kota [1 ]
Kaliappan, Krishna P. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 01期
关键词：
PIPERIDINE; STRATEGIES; SCH725674; CORE;
D O I：
10.1039/c4ob02136c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective total synthesis of Sch-725674, a unique 14-membered macrolactone, has been accomplished in 13 steps. The step-wise dithiane alkylation served as a strategic step to assemble the upper and lower fragments of the molecule, whereas cross metathesis reaction, Yamaguchi macrolactonization and a substrate controlled stereoselective reduction are used as key steps to complete the total synthesis.
引用
收藏
页码：234 / 240
页数：7
相关论文
共 50 条
  • [1] Stereoselective Total Synthesis of Macrolide Sch-725674 and C-7-epi-Sch-725674
    Baikadi, Karunakar
    Talakokkula, Anil
    Narsaiah, A. Venkat
    SYNOPEN, 2019, 3 (01): : 26 - 35
  • [2] A Pot-Economical Approach to the Total Synthesis of Sch-725674
    Bodugam, Mahipal
    Javed, Salim
    Ganguly, Arghya
    Torres, Jessica
    Hanson, Paul R.
    ORGANIC LETTERS, 2016, 18 (03) : 516 - 519
  • [3] First Total Synthesis of Gliomasolide C and Formal Total Synthesis of Sch-725674
    Seetharamsingh, B.
    Khairnar, Pankaj V.
    Reddy, D. Srinivasa
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 290 - 296
  • [4] Enantioselective Modular Total Synthesis of Macrolides Sch725674 and C-4-epi-Sch725674
    Sharma, Brijesh M.
    Gontala, Arjun
    Kumar, Pradeep
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (06) : 1215 - 1226
  • [5] Total Synthesis of Sch 725674
    Vaithegi, Kannan
    Prasad, Kavirayani R.
    TETRAHEDRON, 2018, 74 (20) : 2488 - 2492
  • [6] Total Synthesis of Antifungal Macrolide Sch 725674
    Reddy, Yugendar
    Sabitha, Gowravaram
    CHEMISTRYSELECT, 2016, 1 (10): : 2156 - 2158
  • [7] Enantiospecific Total Synthesis of Macrolactone Sch 725674
    Bali, Amit K.
    Sunnam, Sunil K.
    Prasad, Kavirayani R.
    ORGANIC LETTERS, 2014, 16 (15) : 4001 - 4003
  • [8] Enantioselective synthesis of macrolactone core of the natural product Sch725674
    Sunnam, Sunil Kumar
    Prasad, Kavirayani R.
    TETRAHEDRON, 2014, 70 (12) : 2096 - 2101
  • [9] Enantioselective total synthesis of (+)-SCH 351448
    Crimmins, Michael T.
    Vanier, Grace S.
    ORGANIC LETTERS, 2006, 8 (13) : 2887 - 2890
  • [10] Enantioselective total synthesis of antifungal agent Sch 38516
    Xu, ZM
    Johannes, CW
    Salman, SS
    Hoveyda, AH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) : 10926 - 10927
12345