Enantioselective total syntheses and determination of absolute configuration of marine toxins, oxazinins

被引：5
|
作者：
Dethe, Dattatraya H. [1 ]
Ranjan, Alok [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
RSC ADVANCES | 2013年 / 3卷 / 45期
关键词：
STEREOCHEMISTRY; MUSSELS; DEPROTECTION; BURSATELLIN; ASSIGNMENT;
D O I：
10.1039/c3ra44631j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The enantioselective total syntheses of natural marine toxins, oxazinin-1, -2, -4, -5, -6 and linear precursor preoxazinin-7 are described. The synthetic highlights include Sharpless asymmetric aminohydroxylation and dihydroxylation, oxa-Michael reaction and intramolecular diastereoselective addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine for the construction of the morpholine ring as key steps. The synthetic route also allowed the synthesis of the epi-preoxazinin and a structurally related secondary metabolite bursatellin isolated in 1980 from sea hare Bursatella leachii pleii and its epimer.
引用
收藏
页码：23692 / 23703
页数：12
相关论文
共 50 条
  • [41] Total synthesis of colombiasin A and determination of its absolute configuration
    Nicolaou, K.C.
    Vassilikogiannakis, Georgios
    Mägerlein, Wolfgang
    Kranich, Remo
    2001, Wiley-VCH Verlag (07)
  • [42] Total synthesis and determination of relative and absolute configuration of multiplolide A
    Ramana, C. V.
    Khaladkar, Tushar P.
    Chatterjee, Soumitra
    Gurjar, Mukund K.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10): : 3817 - 3822
  • [43] Total Synthesis and Determination of the Absolute Configuration of Rakicidin C
    Han, Fangzhi
    Liu, Guangju
    Jin, Chaofan
    Wang, Jinghan
    Liu, Jianwei
    Wang, Liang
    Chen, Yue
    ORGANIC LETTERS, 2021, 23 (18) : 7069 - 7073
  • [44] Total synthesis of colombiasin A and determination of its absolute configuration
    Nicolaou, KC
    Vassilikogiannakis, G
    Mägerlein, W
    Kranich, R
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (24) : 5359 - 5371
  • [45] Total synthesis and determination of the absolute configuration of frondosin B
    Inoue, M
    Carson, MW
    Frontier, AJ
    Danishefsky, SJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) : 1878 - 1889
  • [46] Total synthesis and determination of the absolute configuration of (-)-longilene peroxide
    Morimoto, Y
    Iwai, T
    Kinoshita, T
    TETRAHEDRON LETTERS, 2001, 42 (36) : 6307 - 6309
  • [47] Total Synthesis of (-)-Lundurine A and Determination of its Absolute Configuration
    Jin, Shuaijiang
    Gong, Jing
    Qin, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (07) : 2228 - 2231
  • [48] First total synthesis and determination of the absolute configuration of mueggelone
    Motoyoshi, H
    Ishigami, K
    Kitahara, T
    TETRAHEDRON, 2001, 57 (18) : 3899 - 3908
  • [49] Total synthesis and absolute configuration determination of (+)-subincanadine F
    Chen, Pinhong
    Cao, Lidong
    Tian, Wenhai
    Wang, Xinfeng
    Li, Chaozhong
    CHEMICAL COMMUNICATIONS, 2010, 46 (44) : 8436 - 8438
  • [50] Determination of the absolute configuration and the first total synthesis of (-)- and (+)-linderol A
    Yamashita, M
    Shimizu, T
    Kawasaki, I
    Ohta, S
    TETRAHEDRON-ASYMMETRY, 2004, 15 (15) : 2315 - 2317
12345