Synthesis of alkylated indolizidine alkaloids via Pummerer mediated cyclization:: synthesis of (±)-indolizidine 167B, (±)-5-butylindolizidine and (±)-monomorine I

被引:20
|
作者
Kuhakarn, Chutima [1 ]
Seehasombat, Phachanee [1 ]
Jaipetch, Thaworn [2 ]
Pohmakotr, Manat [1 ]
Reutrakul, Vichai [1 ]
机构
[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand
[2] Mahidol Univ, Saiyok 71150, Kanchanaburi, Thailand
关键词
D O I
10.1016/j.tet.2007.12.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of indolizidine alkaloids, i.e., (+/-)-coniceine, (+/-)-indolizidine 167B, (+/-)-5-butylindolizidine and (+/-)-monomorine I via Pummerer cyclization are described. The key step is the transformation of lactam sulfoxide to bicyclic lactam via the Pummerer cyclization. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1663 / 1670
页数:8
相关论文
共 50 条
  • [21] Annulation of a 4-pyrrolylbutanal to a 5,6-dihydroindolizine core:: A novel diastereoselective synthesis of (±)-indolizidine 167B
    Settambolo, R
    Guazzelli, G
    Lazzaroni, R
    LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (02) : 176 - 178
  • [22] Radical cyclization of beta-aminoacrylates: Expedient synthesis of (+)-monomorine 1 and (+)-indolizidine 195B
    Lee, E
    Kang, TS
    Chung, CK
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1996, 17 (03) : 212 - 214
  • [23] Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions:: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine
    Pohmakotr, Manat
    Prateeptongkum, Saisuree
    Chooprayoon, Soontorn
    Tuchinda, Patoomratana
    Reutrakul, Vichai
    TETRAHEDRON, 2008, 64 (10) : 2339 - 2347
  • [24] Intramolecular Schmidt Reaction Involving Primary Azidoalcohols under Nonacidic Conditions: Synthesis of Indolizidine (-)-167B
    Kapat, Ajoy
    Nyfeler, Erich
    Giuffredi, Guy T.
    Renaud, Philippe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) : 17746 - 17747
  • [25] A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (-)-indolizidine 209B
    Song, YC
    Okamoto, S
    Sato, F
    TETRAHEDRON LETTERS, 2002, 43 (48) : 8635 - 8637
  • [26] ASYMMETRIC-SYNTHESIS .2. PRACTICAL METHOD FOR THE ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE ALKALOIDS - TOTAL SYNTHESIS OF (-)-MONOMORINE-I
    ROYER, J
    HUSSON, HP
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05): : 670 - 673
  • [27] Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 20. Asymmetric synthesis of the indolizidine alkaloids monomorine I and indolizidine 223AB
    Momose, T.
    Toshima, M.
    Seki, S.
    Koike, Y.
    Jornal of the Chemical Society. Perkin Transactions 1, (09):
  • [28] A Concise and Diastereoselective Synthesis of Piperidine and Indolizidine Alkaloids via Aza-Prins Cyclization
    Reddy, Basi V. Subba
    Chaya, Dudhmal N.
    Yadav, Jhillu S.
    Gree, Rene
    SYNTHESIS-STUTTGART, 2012, 44 (02): : 297 - 303
  • [29] Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4+2) Cyclization
    Renner, Jonas
    Thakur, Ashish
    Rutz, Philipp M.
    Cowley, Jacob M.
    Evangelista, Judah L.
    Kumar, Puneet
    Prater, Matthew B.
    Stolley, Ryan M.
    Louie, Janis
    ORGANIC LETTERS, 2020, 22 (03) : 924 - 928
  • [30] Epoxide-initiated electrophilic cyclization of azides:: A novel route for the stereloselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D
    Reddy, PG
    Varghese, B
    Baskaran, S
    ORGANIC LETTERS, 2003, 5 (04) : 583 - 585