Total synthesis of (-)-δ-lycorane

被引：0
|
作者：
Shukla, Jyoti [1 ,2 ]
Gangwar, Manoj Kumar [3 ]
Koley, Dipankar [1 ,2 ]
机构：
[1] CSIR, Med & Proc Chem Div, Cent Drug Res Inst, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] Univ Allahabad, Dept Chem, Fac Sci, Prayagraj 211002, Uttar Pradesh, India
来源：
NEW JOURNAL OF CHEMISTRY | 2023年 / 47卷 / 41期
关键词：
ASYMMETRIC TOTAL-SYNTHESIS; STEREOSELECTIVE C-C; ALKALOIDS; HYDROGENATION; EFFICIENT; ACCESS; STEREOCHEMISTRY; CYCLIZATION; COMPLEXES; ALDEHYDES;
D O I：
10.1039/d3nj03567k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The total synthesis of (-)-delta-lycorane is reported. We performed organocatalytic Mannich reaction between phenylacetaldehyde and gamma-hydroxy lactam to construct a 5-substituted-2-pyrrolidone derivative in favor of the cis-isomer. Furthermore, diastereoselective conjugate addition to alpha,beta-unsaturated lactam was accomplished to obtain 4,5-disubstituted-2-pyrrolidone. The other salient features of this synthesis include Bischler-Napieralski reaction and ring closing metathesis. The total synthesis of (-)-delta-lycorane is reported.
引用
收藏
页码：18900 / 18904
页数：5
相关论文
共 50 条
  • [1] Catalytic, Asymmetric Total Synthesis of (+)-?-, (+)-?-, (+)-?-, and(-)-?-Lycorane
    Zhang, Tian-Yuan
    Zhang, Lu-Yue
    Liang, Xiao
    Wei, Kun
    Yang, Yu-Rong
    ORGANIC LETTERS, 2022, 24 (15) : 2905 - 2909
  • [2] Asymmetric total synthesis of (-)-δ-lycorane
    Wang, Junliang
    Li, Jianneng
    Shen, Xianwang
    Dong, Cong
    Lin, Jun
    Wei, Kun
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06): : 1149 - 1152
  • [3] Catalytic Asymmetric Hydrogenation of α-Arylcyclohexanones and Total Synthesis of (-)-α-Lycorane
    Li, Gang
    Xie, Jian-Hua
    Hou, Jing
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) : 1597 - 1604
  • [4] Asymmetric Total Syntheses of (-)--Lycorane, (-)-Zephyranthine, and Formal Synthesis of (+)-Clivonine
    Chen, Yong-Jian
    Cai, Sen-Lin
    Wang, Chuan-Chuan
    Cheng, Jin-Duo
    Kramer, Soren
    Sun, Xing-Wen
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (12) : 1309 - 1313
  • [5] Extension of hydrogen borrowing alkylation reactions for the total synthesis of (-)-γ-lycorane
    Hall, Christopher J. J.
    Marriott, Indi S.
    Christensen, Kirsten E.
    Day, Aaron J.
    Goundry, William R. F.
    Donohoe, Timothy J.
    CHEMICAL COMMUNICATIONS, 2022, 58 (32) : 4966 - 4968
  • [6] Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpynoline
    Huntley, Raymond J.
    Funk, Raymond L.
    TETRAHEDRON LETTERS, 2011, 52 (50) : 6671 - 6674
  • [7] Total synthesis of (+)-γ-lycorane from ethyl lactate using iterative Claisen and Overman rearrangement reactions
    Uphade, Manoj B.
    Prasad, Kavirayani R.
    TETRAHEDRON, 2020, 76 (46)
  • [8] Total Syntheses of (±)-α-Lycorane and (±)-1-Deoxylycorine
    Jung, Yong-Geun
    Lee, Sang-Choul
    Cho, Hyun-Kyu
    Darvatkar, Nitin B.
    Song, Ji-Young
    Cho, Cheon-Gyu
    ORGANIC LETTERS, 2013, 15 (01) : 132 - 135
  • [9] An efficient palladium mediated synthesis of (±)-γ-lycorane
    Shao, ZH
    Chen, JB
    Huang, R
    Wang, CY
    Li, L
    Zhang, HB
    SYNLETT, 2003, (14) : 2228 - 2230
  • [10] Progress towards the Total Syntheses of Amaryllidaceae Alkaloids γ-Lycorane
    Xiao, Jie
    Zhou, Guang-Hua
    Zhou, An-Xi
    Ji, Cong-Bin
    CHEMISTRY & BIODIVERSITY, 2022, 19 (09)
12345