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
  • [1] Total Synthesis of Pyrrole-Imidazole Alkaloid (+)-Cylindradine B
    Iwata, Makoto
    Kamijoh, Yuko
    Yamamoto, Eri
    Yamanaka, Masahiro
    Nagasawa, Kazuo
    ORGANIC LETTERS, 2017, 19 (02) : 420 - 423
  • [2] FUNEBRAL, A NEW PYRROLE LACTONE ALKALOID FROM QUARARIBEA-FUNEBRIS
    ZENNIE, TM
    CASSADY, JM
    RAFFAUF, RF
    JOURNAL OF NATURAL PRODUCTS, 1986, 49 (04): : 695 - 698
  • [3] A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A
    Duspara, Petar A.
    Batey, Robert A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) : 10862 - 10866
  • [4] FUNEBRADIOL, A NEW PYRROLE LACTONE ALKALOID FROM QUARARIBEA-FUNEBRIS FLOWERS
    ZENNIE, TM
    CASSADY, JM
    JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06): : 1611 - 1614
  • [5] SESQUITERPENE LACTONE TOTAL SYNTHESIS
    GRIECO, PA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 51 - 51
  • [6] SYNTHESIS OF TRITIATED SENECIOYL DEHYDRORETRONECINE, A PYRROLIZIDINE ALKALOID PYRROLE
    SHUMAKER, RC
    HSIA, MTS
    SEYMOUR, JL
    ALLEN, JR
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1978, 15 : 227 - 232
  • [7] Total Synthesis of a Pyrroloindoloquinazoline Alkaloid
    Gahtory, Digvijay
    Chouhan, Mangilal
    Sharma, Ratnesh
    Nair, Vipin A.
    ORGANIC LETTERS, 2013, 15 (15) : 3942 - 3945
  • [8] Complex alkaloid total synthesis
    Movassaghi, Mohammad
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [9] Total Synthesis of the Zoanthamine Alkaloid
    M.Miyashita
    复旦学报(自然科学版), 2005, (05) : 171 - 172
  • [10] Complex alkaloid total synthesis
    Movassaghi, Mohammad
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240