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 [J].
Arimoto, H ;
Hayakawa, I ;
Kuramoto, M ;
Uemura, D .
TETRAHEDRON LETTERS, 1998, 39 (08) :861-862
[2]   REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES [J].
BRANDI, A ;
DURUST, Y ;
CORDERO, FM ;
DESARLO, F .
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 [J].
Chou, T ;
Kuramoto, M ;
Otani, Y ;
Shikano, M ;
Yazawa, K ;
Uemura, D .
TETRAHEDRON LETTERS, 1996, 37 (22) :3871-3874
[4]   A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines [J].
Ciblat, S ;
Besse, P ;
Canet, JL ;
Troin, Y ;
Veschambre, H ;
Gelas, J .
TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2225-2235
[5]   A simple synthesis of (+)- and (-)-alkaloid 241D and C-4 epimers [J].
Ciblat, S ;
Calinaud, P ;
Canet, JL ;
Troin, Y .
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 [J].
Clive, DLJ ;
Yeh, VSC .
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] [J].
Comoy, C ;
Marot, C ;
Podona, T ;
Baudin, ML ;
MorinAllory, L ;
Guillaumet, G ;
Pfeiffer, B ;
Caignard, DH ;
Renard, P ;
Rettori, MC ;
Adam, G ;
GuardiolaLemaitre, B .
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 [J].
HEATHCOCK, CH ;
DAVIDSEN, SK ;
MILLS, SG ;
SANNER, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2531-2544
[10]   Synthesis and antiviral activity evaluation of some new aminoadamantane derivatives .2. [J].
Kolocouris, N ;
Kolocouris, A ;
Foscolos, GB ;
Fytas, G ;
Neyts, J ;
Padalko, E ;
Balzarini, J ;
Snoeck, R ;
Andrei, G ;
DeClercq, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3307-3318