Total Synthesis of Ellipticine Quinones, Olivacine, and Calothrixin B

被引:57
|
作者
Ramkumar, Nagarajan [1 ]
Nagarajan, Rajagopal [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 02期
关键词
FRIEDEL-CRAFTS HYDROXYALKYLATION; INDOLE-2,3-DICARBOXYLIC ANHYDRIDE; EFFICIENT SYNTHESIS; DIRECTED ORTHO; PHASE-II; METALATION; DERIVATIVES; CANCER; ALKALOIDS; PYRIDINES;
D O I
10.1021/jo402593w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct route to the synthesis of biologically active ellipticine quinones, olivacine, and calothrbcin B is described. The prominent key steps involved are Friedel-Crafts hydroxyalkylation followed by oxidation and directed ortho-lithiation reactions of readily available indole-2-carboxylate esters with appropriately substituted pyridine and quinoline carboxaldehydes.
引用
收藏
页码:736 / 741
页数:6
相关论文
共 50 条
  • [1] Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine
    Barrera, Edson
    Israel Hernandez-Benitez, R.
    Gonzalez-Gonzalez, Carlos A.
    Escalante, Carlos H.
    Fuentes-Benites, Aydee
    Gonzalez-Romero, Carlos
    Becerra-Martinez, Elvia
    Delgado, Francisco
    Tamariz, Joaquin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (24)
  • [2] Total Synthesis of Olivacine and Ellipticine via a Lactone Ring Opening and Aromatization Cascade
    Dilek, Omer
    Patir, Suleyman
    Tilki, Tahir
    Erturk, Erkan
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7901 - 7916
  • [3] An efficient total synthesis of calothrixin B
    Bhosale, Shrikar M.
    Gawade, Rupesh L.
    Puranik, Vedavati G.
    Kusurkar, Radhika S.
    TETRAHEDRON LETTERS, 2012, 53 (23) : 2894 - 2896
  • [4] PYRIDOCARBAZOLE ALKALOIDS - SYNTHESIS OF OLIVACINE AND ELLIPTICINE ANALOGS
    WIJSMULLER, WFA
    WANNER, MJ
    KOOMEN, GJ
    PANDIT, UK
    HETEROCYCLES, 1986, 24 (07) : 1795 - 1797
  • [5] Total Synthesis of Calothrixin B and Its Analogs
    Saravanan, Velu
    Ramalingam, Bose Muthu
    Mohanakrishnan, Arasambattu K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (06) : 1266 - 1279
  • [6] Synthesis of precursors of linear thienocarbazole analogues of ellipticine and olivacine
    Peixoto, FMC
    Queiroz, MJRP
    Kirsch, G
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (04): : 172 - 173
  • [7] Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B
    Mori-Quiroz, Luis M.
    Dekarske, Madeline M.
    Prinkki, Austin B.
    Clift, Michael D.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12257 - 12266
  • [8] Application of alkylquinone tautomerization to the total synthesis of Calothrixin B
    Quiroz, Luis Mori
    Dekarske, Madeline
    Clift, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] A synthesis of calothrixin B
    Sissouma, D
    Collet, SC
    Guingant, AY
    SYNLETT, 2004, (14) : 2612 - 2614
  • [10] Recent Progress Towards the Total Synthesis and Biological Studies of Calothrixin A and B
    Parvatkar, Prakash T.
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (08) : 839 - 855