First Total Synthesis of Pandamarine

被引:34
|
作者
Kalaitzakis, Dimitris [1 ]
Noutsias, Dimitris [1 ]
Vassilikogiannakis, Georgios [1 ]
机构
[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece
基金
欧洲研究理事会;
关键词
AUS SCHIZOZYGIA CAFFAEOIDES; ONE-POT SYNTHESIS; PANDANUS-AMARYLLIFOLIUS; SINGLET-OXYGEN; SIMPLE FURANS; INDOLE ALKALOIDS; HAPLOPHYTINE;
D O I
10.1021/acs.orglett.5b01693
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of pandamarine, an alkaloid isolated from Pandanus amaryllifolius is reported. The key step of this extremely short (six steps in total) and protecting group-free synthesis is a highly efficient cascade reaction sequence initiated by the photooxidation of an easily accessible, and symmetric difuran precursor.
引用
收藏
页码:3596 / 3599
页数:4
相关论文
共 50 条
  • [1] First total synthesis of (±)-tangutorine
    Putkonen, T
    Tolvanen, A
    Jokela, R
    TETRAHEDRON LETTERS, 2001, 42 (37) : 6593 - 6594
  • [2] First Total Synthesis of Paracaseolide A
    Noutsias, Dimitris
    Vassilikogiannakis, Georgios
    ORGANIC LETTERS, 2012, 14 (14) : 3565 - 3567
  • [3] First Total Synthesis of (±)-Elatadihydrochalcone and Its Derivatives
    Xia, Likai
    Lee, Yong Rok
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (06): : 2087 - 2090
  • [4] First Total Synthesis of 7-Isovaleryloxy-8-methoxygirinimbine
    Bruetting, Christian
    Schmidt, Arndt W.
    Kataeva, Olga
    Knoelker, Hans-Joachim
    SYNTHESIS-STUTTGART, 2018, 50 (13): : 2516 - 2522
  • [5] First Synthesis of Benzopyridoiodolium Salts and Twofold Buchwald-Hartwig Amination for the Total Synthesis of Quindoline
    Letessier, Julien
    Detert, Heiner
    SYNTHESIS-STUTTGART, 2012, 44 (02): : 290 - 296
  • [6] Efficient Synthesis of Bibenzyl Derivatives Bearing Pyranyl Moieties: First Total Synthesis of Bauhinol D
    Park, Byung Ho
    Lee, Yong Rok
    Kim, Sung Hong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (02): : 566 - 570
  • [7] On Demand Synthesis of C3-N1' Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)-Rivularin A
    Tokushige, Keisuke
    Abe, Takumi
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (11)
  • [8] Total synthesis of angelone enabled by a remarkable biomimetic sequence
    Tan, Haibo
    Chen, Xinzheng
    Liu, Zheng
    Wang, David Zhigang
    TETRAHEDRON, 2012, 68 (21) : 3952 - 3955
  • [9] Total synthesis of (-)-muricatacin
    Gonzalez, Maria
    Gandara, Zoila
    Covelo, Berta
    Gomez, Generosa
    Fall, Yagamare
    TETRAHEDRON LETTERS, 2011, 52 (45) : 5983 - 5986
  • [10] Total synthesis of aspidophytine
    Marino, Joseph P.
    Cao, Ganfeng
    TETRAHEDRON LETTERS, 2006, 47 (44) : 7711 - 7713