Synthesis of Two Unnatural Oxygenated Aaptaminoids

被引:9
|
作者
Abbiati, Giorgio [1 ]
Doda, Arjana [1 ]
Dell'Acqua, Monica [1 ]
Pirovano, Valentina [1 ]
Facoetti, Diego [1 ]
Rizzato, Silvia [2 ]
Rossi, Elisabetta [1 ]
机构
[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ A Marchesini, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期
关键词
MODIFIED CURTIUS REACTION; ALPHA-BLOCKING ACTIVITY; CONVENIENT REAGENT; MARINE ALKALOIDS; DERIVATIVES; CYCLIZATION; ANALOGS; 4(1H)-QUINOLONES; ISOQUINOLINES; ISOAAPTAMINE;
D O I
10.1021/jo3020598
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.
引用
收藏
页码:10461 / 10467
页数:7
相关论文
共 50 条
  • [1] Straightforward synthesis of unnatural poly-oxygenated steroid sapogenins
    Rosado Abon, Anielka
    Iglesias-Arteaga, Martin A.
    ARKIVOC, 2021,
  • [2] Cyclization Approaching to (-)-Lycojapodine A: Synthesis of Two Unnatural Alkaloids
    Yang, Yu-Rong
    Shen, Liang
    Wei, Kun
    Zhao, Qin-Shi
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (04): : 1317 - 1320
  • [3] Triumph for unnatural synthesis
    Stéphane Quideau
    Nature, 2011, 474 : 459 - 460
  • [4] UNNATURAL PRODUCT SYNTHESIS
    STODDART, JF
    NATURE, 1988, 334 (6177) : 10 - 11
  • [5] SYNTHESIS OF OXYGENATED RETINOIDS
    SINGH, AK
    SYNTHETIC COMMUNICATIONS, 1983, 13 (11) : 919 - 925
  • [6] SYNTHESIS OF OXYGENATED COUMESTANS
    RANI, BSU
    DARBARWAR, M
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1986, 63 (12) : 1060 - 1062
  • [7] Unnatural α-amino acid synthesis
    Trinh, Tuan Anh
    Schomaker, Jennifer M.
    NATURE SYNTHESIS, 2023, 2 (07): : 600 - 601
  • [8] SYNTHESIS OF NATURAL AND UNNATURAL FRONTALIN
    HOSOKAWA, T
    MAKABE, Y
    SHINOHARA, T
    MURAHASHI, SI
    CHEMISTRY LETTERS, 1985, (10) : 1529 - 1530
  • [9] SYNTHESIS OF THE UNNATURAL ENANTIOMER OF CHOLESTEROL
    MICKUS, DE
    RYCHNOVSKY, SD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 101 - ORGN
  • [10] Stereoselectivity in the synthesis of unnatural disaccharides
    Kniezo, L
    Budesínsky, M
    Vojtísek, A
    Martinková, M
    ENANTIOMER, 1999, 4 (3-4): : 351 - 362