Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-Endo selective cyclization

被引：27
|
作者：
Taniguchi, T
Tamura, O
Uchiyama, M
Muraoka, O
Tanabe, G
Ishibashi, H [1 ]
机构：
[1] Kanazawa Univ, Div Pharmaceut Sci, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan
[2] Kinki Univ, Fac Pharmaceut Sci, Osaka 5770818, Japan
来源：
SYNLETT | 2005年 / 07期
关键词：
cyclizations; cylindricine; regioselectivity; radical cascade; acyl radical;
D O I：
10.1055/s-2005-865236
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
On treatment with Bu3SnH and azobis(cyclohexanecarbonitrile) (ACN), enamide 19 underwent a 6-endo-trig/5-endo-trig radical cascade to afford perhydropyrrolo[2.1-j]quinoline derivative 21, a cylindricine skeleton.
引用
收藏
页码：1179 / 1181
页数：3
相关论文
共 50 条
  • [1] SYNTHESIS OF (+/-)-TRIMETHYLPELTOGYNOL VIA 6-ENDO RADICAL CYCLIZATION
    AHMADJUNAN, SA
    WHITING, DA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02): : 418 - 419
  • [2] 6-endo,6-endo,6-exo cascade cyclization starting from vinyl radical;: construction of a dodecahydrophenanthrene system
    Takasu, K
    Kuroyanagi, J
    Katsumata, A
    Ihara, M
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6277 - 6280
  • [3] Marrying Iterative Synthesis to Cascading Radical Cyclization: 6-endo/5-exo Radical Cascade across Bis-Vinyl Ethers
    Davies, Katherine A.
    Wulff, Jeremy E.
    ORGANIC LETTERS, 2011, 13 (20) : 5552 - 5555
  • [4] Cascade radical cyclization of polyolefinic vinyl iodides:: comparison between 5-exo and 6-endo cyclization of vinyl radicals
    Maiti, S
    Takasu, K
    Katsumata, A
    Kuroyanagi, J
    Ihara, M
    ARKIVOC, 2002, : 197 - 211
  • [5] 6-endo versus 5-exo radical cyclization:: streamlined syntheses of carbahexopyranoses and derivatives by 6-endo-trig radical cyclization
    Gomez, Ana M.
    Company, Maria D.
    Uriel, Clara
    Valverde, Serafin
    Lopez, J. Cristobal
    TETRAHEDRON LETTERS, 2007, 48 (09) : 1645 - 1649
  • [6] Photochemical Radical Cascade 6-endo Cyclization of Dienes with α-Carbonyl Bromides for the Synthesis of Six-Membered Benzo-Fused Lactams
    Sui, Jia-Li
    Guo, Yang
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Huang, Peng-Fei
    Liu, Yu
    Li, Jin-Heng
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (19) : 2323 - 2328
  • [7] RATE CONSTANTS FOR ARYL RADICAL CYCLIZATION TO ALDIMINES - SYNTHESIS OF TETRAHYDROISOQUINOLINES BY FAST 6-ENDO CLOSURES TO CARBON
    TOMASZEWSKI, MJ
    WARKENTIN, J
    TETRAHEDRON LETTERS, 1992, 33 (16) : 2123 - 2126
  • [8] Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines
    Ryu, I
    Ogura, S
    Minakata, S
    Komatsu, M
    TETRAHEDRON LETTERS, 1999, 40 (08) : 1515 - 1518
  • [9] Concise synthesis of the chemopreventitive agent (±)-deguelin via a key 6-endo hydroarylation
    Pastine, SJ
    Sames, D
    ORGANIC LETTERS, 2003, 5 (22) : 4053 - 4055
  • [10] Radical cascade involving a 5-endo-trig cyclization of α-amidoyl radicals
    Ishibashi, H
    Ishita, A
    Tamura, O
    TETRAHEDRON LETTERS, 2002, 43 (03) : 473 - 475
12345