tert-butoxycarbamate group:: a useful protecting group for the synthesis of orthogonally protected 'tropane-like' scaffolds

被引:8
作者
Paparin, JL [1 ]
Crévisy, C [1 ]
Grée, R [1 ]
机构
[1] Ecole Natl Super Chim Rennes, CNRS, Lab Synth & Activat Biomol, F-35700 Rennes, France
关键词
4+3] cycloaddition; combinatorial chemistry; protecting groups; tropanes;
D O I
10.1016/S0040-4039(00)00198-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of N-Boc-protected tropanes by a [4+3] cycloaddition reaction is described. The Boc group has been cleanly removed demonstrating that this group would be very useful for the synthesis of 'tropane-like' scaffolds for combinatorial chemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2343 / 2346
页数:4
相关论文
共 12 条
[1]  
[Anonymous], 1997, Organic Reactions
[2]  
CHAIKEN IM, 1996, MOL DIVERSITY COMBIN
[3]  
DODA M, 1963, ARCH INT PHARMACOD T, V145, P264
[4]   NEW TROPINONE SYNTHESIS [J].
FIERZ, G ;
CHIDGEY, R ;
HOFFMANN, HM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) :410-411
[5]   CARBON-CARBON BOND FORMATION PROMOTED BY TRANSITION-METAL CARBONYLS .19. GENERAL SYNTHESIS OF TROPANE ALKALOIDS VIA POLYBROMO KETONE-IRON CARBONYL REACTION [J].
HAYAKAWA, Y ;
BABA, Y ;
MAKINO, S ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1786-1791
[6]   THE CYCLOADDITION OF ALLYL CATIONS TO 1,3-DIENES - GENERAL-METHOD FOR THE SYNTHESIS OF 7-MEMBERED CARBOCYCLES [J].
HOFFMANN, HMR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :1-19
[7]   Palladium-mediated three-component coupling strategy for the solid-phase synthesis of tropane derivatives [J].
Koh, JS ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4494-4495
[8]  
Lounasmaa M., 1993, ALKALOIDS, V44, P1, DOI DOI 10.1016/S0099-9598(08)60143-1
[9]   AN EFFICIENT ROUTE TO THE TROPANE ALKALOIDS [J].
MANN, J ;
BARBOSA, LCD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :787-790
[10]   Syntheses of new open-ring and homo-epibatidine analogues from tropinone [J].
Olivo, HF ;
Colby, DA ;
Hemenway, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4966-4968