A new route to 2-spiropiperidines

被引:22
作者
Ciblat, S [1 ]
Canet, JL [1 ]
Troin, Y [1 ]
机构
[1] Univ Blaise Pascal, Ecole Natl Super Chim Clemont Ferrand, Lab Chim Heterocylces & Glucides, F-63174 Aubiere, France
关键词
D O I
10.1016/S0040-4039(01)00881-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An intramolecular Mannich reaction, involving cyclanones together with a ketoprotected aminobutanone in the presence of a Lewis acid, is employed to prepare rapidly 2,2 ' -spiropiperidine skeletons. Phis approach is validated through a concise and efficient synthesis of spiro [piperidine-2,2 ' -adamantane] 4, an antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4815 / 4817
页数:3
相关论文
共 19 条
  • [1] Absolute stereochemistry of halichlorine; A potent inhibitor of VCAM-1 induction
    Arimoto, H
    Hayakawa, I
    Kuramoto, M
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1998, 39 (08) : 861 - 862
  • [2] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES
    BRANDI, A
    DURUST, Y
    CORDERO, FM
    DESARLO, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) : 5666 - 5670
  • [3] Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata
    Chou, T
    Kuramoto, M
    Otani, Y
    Shikano, M
    Yazawa, K
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1996, 37 (22) : 3871 - 3874
  • [4] A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines
    Ciblat, S
    Besse, P
    Canet, JL
    Troin, Y
    Veschambre, H
    Gelas, J
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (11) : 2225 - 2235
  • [5] A simple synthesis of (+)- and (-)-alkaloid 241D and C-4 epimers
    Ciblat, S
    Calinaud, P
    Canet, JL
    Troin, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03): : 353 - 357
  • [6] Synthesis of a 6-azaspiro[4.5]decane related to halichlorine and the pinnaic acids
    Clive, DLJ
    Yeh, VSC
    [J]. TETRAHEDRON LETTERS, 1999, 40 (49) : 8503 - 8507
  • [7] 3-amino-3,4-dihydro-2H-1-benzopyran derivatives as 5-HT1A receptor ligands and potential anxiolytic agents .2. Synthesis and quantitative structure-activity relationship studies of spiro[pyrrolidine- and piperidine-2,3'(2'H)-benzopyrans]
    Comoy, C
    Marot, C
    Podona, T
    Baudin, ML
    MorinAllory, L
    Guillaumet, G
    Pfeiffer, B
    Caignard, DH
    Renard, P
    Rettori, MC
    Adam, G
    GuardiolaLemaitre, B
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) : 4285 - 4298
  • [8] Daly JW, 1999, ALKAL CHEM, V13, P1, DOI 10.1016/S0735-8210(99)80024-7
  • [9] DAPHNIPHYLLUM ALKALOIDS .10. CLASSICAL TOTAL SYNTHESIS OF METHYL HOMODAPHNIPHYLLATE
    HEATHCOCK, CH
    DAVIDSEN, SK
    MILLS, SG
    SANNER, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2531 - 2544
  • [10] Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives .2.
    Kolocouris, N
    Kolocouris, A
    Foscolos, GB
    Fytas, G
    Neyts, J
    Padalko, E
    Balzarini, J
    Snoeck, R
    Andrei, G
    DeClercq, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) : 3307 - 3318