Total Synthesis of a Pyrrole Lactone Alkaloid, Longanlactone

被引:18
作者
Reddy, Chada Raji [1 ]
Reddy, Motatipally Damoder [1 ]
Dilipkumar, Uredi [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500607, Andhra Pradesh, India
关键词
Total synthesis; Alkaloids; Nitrogen heterocycles; Lactones; Amino acids; NATURAL-PRODUCTS; QUARARIBEA METABOLITES; PROPARGYLATION; (-)-FUNEBRINE;
D O I
10.1002/ejoc.201402563
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric total synthesis of the natural pyrrole lactone longanlactone has been achieved. The key reactions, a Barbier propargylation and a Paal-Knorr pyrrole synthesis, have provided easy access to the target natural product from L-aspartic acid in six steps and 31% overall yield. The C-4 epimer of the natural product and propionyllonganlactone have also been prepared by this strategy.
引用
收藏
页码:6310 / 6313
页数:4
相关论文
共 50 条
  • [31] Enantioselective total synthesis of the polycyclic guanidine-containing marine alkaloid (-)-batzelladine D
    Evans, P. Andrew
    Qin, Jun
    Robinson, John E.
    Bazin, Berangere
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) : 7417 - 7419
  • [32] Total synthesis of the naphthyridine alkaloid jasminine
    Bennasar, ML
    Roca, T
    Zulaica, E
    Monerris, M
    TETRAHEDRON, 2004, 60 (32) : 6785 - 6789
  • [33] N-Alkynyl Pyrrole Based Total Synthesis of Shensongine A
    Reinus, Brandon J.
    Kerwin, Sean M.
    SYNTHESIS-STUTTGART, 2019, 51 (21): : 4085 - 4105
  • [34] Total Synthesis and Structural Reassignment of the -Lactone Polyketide from Diaporthe sp SXZ-19
    Yadav, Jhillu S.
    Dutta, Palash
    Ganganna, Bogonda
    Srinivas, Eedubilli
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (31) : 6891 - 6899
  • [35] Total synthesis of akuammiline alkaloid (+)-strictamine
    Chen, Zhi-Tao
    Xiao, Tao
    Tang, Pei
    Zhang, Dan
    Qin, Yong
    TETRAHEDRON, 2018, 74 (11) : 1129 - 1134
  • [36] Total synthesis of a piperidine alkaloid, microcosamine A
    Reddy, Chada Raji
    Latha, Bellamkonda
    Warudikar, Kamalkishor
    Singarapu, Kiran Kumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (01) : 251 - 258
  • [37] Total synthesis of tetrahydroquinoline alkaloid (+)-angustureine
    Lin, XF
    Li, Y
    Ma, DW
    CHINESE JOURNAL OF CHEMISTRY, 2004, 22 (09) : 932 - 934
  • [38] Total Synthesis of Carbazole Alkaloid Murrayaquinone A
    Zhang, Kun
    Xu, Hongjin
    Liu, Zibo
    Song, Chuanjun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (04) : 1142 - 1146
  • [39] Total Synthesis of Tetrahydroquinoline Alkaloid (+)-Angustureine
    林宪峰
    李瑜
    马大为
    ChineseJournalofChemistry, 2004, (09) : 932 - 934
  • [40] A total synthesis of subarine, a marine alkaloid related to the pyridoacridine family
    Bijeire, L
    Legentil, L
    Bastide, J
    Darro, F
    Rochart, C
    Delfourne, E
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) : 1891 - 1893