Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one

被引：40
|
作者：
Socha, D [1 ]
Jurczak, M [1 ]
Chmielewski, M [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
CARBOHYDRATE RESEARCH | 2001年 / 336卷 / 04期
关键词：
1,3-dipolar cycloaddition; (3S)-tert-butoxy-1-pyrroline N-oxide; 7-hydroxylentiginosine;
D O I：
10.1016/S0008-6215(01)00265-8
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
(1aR,5aR,5bS,6S,7S)-6,7-Di-tert-butoxy-5-oxo-pyrrolidino[1,2-b]isoxazolidino[4,5-c]tetrahydropyran (8) prepared by (1,3)-dipolar cycloaddition of the cyclic nitrone 6 derived from tartaric acid to 5,6-dihydro-2H-pyran-2-one (7) was transformed into indolizidine 11 via a. sequence of reactions involving methanolysis of the lactone ring, intramolecular alkylation of the nitrogen atom promoted by a carbontetrabromide-triphenylphosphine mixture and hydrogenolysis of the N-O bond. Decarboxylation of 11 provided known 7-hydroxylentiginosine derivative 14, whereas oxidative decarboxylation gave indolizidine 15 structurally related to castanospermine. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：315 / 318
页数：4
相关论文
共 50 条
  • [31] 5-Hydroxy-6-[(E)-2-phenylethenyl]-5,6dihydro-2H-pyran-2-one isolated from Goniothalamus ridleyi
    Jusoh, Samsiah
    Din, Laily B.
    Zakaria, Zuriati
    Khaledi, Hamid
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2274 - +
  • [32] Identification of Cyclic Dipeptides and a New Compound (6-(5-Hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one) Produced by Streptomyces fungicidicus against Alternaria solani
    Liu, He
    An, Mengnan
    Si, Hongyang
    Shan, Yuhang
    Xu, Chuantao
    Hu, Gang
    Xie, Yunbo
    Liu, Dongyang
    Li, Shujun
    Qiu, Rui
    Zhang, Chong
    Wu, Yuanhua
    MOLECULES, 2022, 27 (17):
  • [33] DERIVATIVES OF 5,6-DIHYDRO-2H-PYRAN-3-CARBOXYLIC ACID
    SPREITZER, H
    MULLER, P
    BUCHBAUER, G
    MONATSHEFTE FUR CHEMIE, 1990, 121 (11): : 963 - 970
  • [34] NOVEL REDUCTIVE OPENING OF 5,6-DIHYDRO-2H-PYRAN RING
    JURCZAK, J
    BAUER, T
    ANKNER, K
    HETEROCYCLES, 1986, 24 (06) : 1531 - 1534
  • [35] IMPROVED PROCEDURES FOR PREPARATION OF TETRAHYDRO-4H-PYRAN-4-ONE AND 5,6-DIHYDRO-4-METHOXY-2H-PYRAN
    ARENTZEN, R
    KUI, YTY
    REESE, CB
    SYNTHESIS-STUTTGART, 1975, (08): : 509 - 510
  • [36] 5,6-Dimethyl-4-phenyl-2H-pyran-2-one
    Xu, Hai-Yun
    Guo, Sheng-Hai
    Li, Kun
    Fan, Xue-Sen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1131 - +
  • [37] 5,6-DIHYDRO-2H-PYRAN-2-ONES AS NOVEL HIV PROTEASE INHIBITORS
    HAGEN, SE
    DOMAGALA, JM
    ELLSWORTH, EL
    FERGUSON, D
    LUNNEY, EA
    TAIT, BD
    TUIT, BD
    TUMMINO, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 22 - MEDI
  • [38] DERIVATIVES OF 2-ALKOXY-5,6-DIHYDRO-2H-PYRAN AS SUBSTRATES IN SYNTHESIS OF MONOSACCHARIDES .24. SYNTHESIS OF 6-ACYL DERIVATIVES FROM 6-CYANO-2-METHOXY-5,6-DIHYDRO-2H-PYRAN
    BELNIAK, K
    ZAMOJSKI, A
    ROCZNIKI CHEMII, 1977, 51 (7-8): : 1545 - 1547
  • [39] A one-pot efficient synthesis of highly functionalized 5,6-dihydronaphthalenes from 2H-pyran-2-one
    Sil, D
    Ram, VJ
    TETRAHEDRON LETTERS, 2005, 46 (30) : 5013 - 5015
  • [40] SYNTHESIS OF 5,6-DIHYDRO-2H-THIOPYRANS
    CHEN, CH
    REYNOLDS, GA
    ZUMBULYADIS, N
    VANALLAN, JA
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (02) : 289 - 291
12345