New synthesis of SKF 89976A

被引:8
作者
Chang, Meng-Yang [1 ]
Wang, Si-Yun
Pai, Chun-Li
机构
[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
3-hydroxypiperidine; Baeyer-Villiger lactonization; 3-tosyl-[1,3]oxazepan-7-one; 4,4-diaryl-3-butenyl-1-amines;
D O I
10.1016/j.tetlet.2006.06.156
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted 4,4-diaryl-3-butenyl-l-amines are synthesized in nearly 34-47% overall yields starting from 3-hydroxypiperidine by the regioselective Baeyer-Villiger lactonization, Grignard addition and elimination sequence. This facile strategy was also used to synthesize racemic SKF 89976A. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6389 / 6392
页数:4
相关论文
共 42 条
[1]   PREPARATION OF METHYL-2-(OMEGA-IODOALKYL)PROPENOATES AND A FACILE ROUTE TO 2-CARBOMETHOXY-1,3-BUTADIENE [J].
ALANINE, AID ;
FISHWICK, CWG ;
JONES, AD ;
MITCHELL, MB .
TETRAHEDRON LETTERS, 1989, 30 (41) :5653-5654
[2]   INTRAMOLECULAR [3+2] CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE IMIDATE-METHYLIDES [J].
ALANINE, AID ;
FISHWICK, CWG .
TETRAHEDRON LETTERS, 1989, 30 (33) :4443-4446
[3]   ORALLY ACTIVE AND POTENT INHIBITORS OF GAMMA-AMINOBUTYRIC ACID UPTAKE [J].
ALI, FE ;
BONDINELL, WE ;
DANDRIDGE, PA ;
FRAZEE, JS ;
GARVEY, E ;
GIRARD, GR ;
KAISER, C ;
KU, TW ;
LAFFERTY, JJ ;
MOONSAMMY, GI ;
OH, HJ ;
RUSH, JA ;
SETLER, PE ;
STRINGER, OD ;
VENSLAVSKY, JW ;
VOLPE, BW ;
YUNGER, LM ;
ZIRKLE, CL .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (05) :653-660
[4]   N-LITHIO-N-(2-LITHIOETHYL)BENZAMIDE AND N-LITHIO-N-(3-LITHIOPROPYL)BENZAMIDE - DIRECT PREPARATION AND SYNTHETIC APPLICATIONS OF 2-LITHIOETHYL-AMINE AND 3-LITHIOPROPYL-AMINE EQUIVALENTS [J].
BARLUENGA, J ;
FOUBELO, F ;
FANANAS, FJ ;
YUS, M .
TETRAHEDRON, 1989, 45 (07) :2183-2192
[5]   ARENE IMINIUM SALT ELECTRON-TRANSFER PHOTOCHEMISTRY - MECHANISTICALLY INTERESTING PHOTOADDITION PROCESSES [J].
BORG, RM ;
HEUCKEROTH, RO ;
LAN, AJY ;
QUILLEN, SL ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2728-2737
[6]   UNPRECEDENTED INTRA- AND INTERMOLECULAR PALLADIUM-CATALYZED COUPLING REACTIONS WITH METHYLENECYCLOPROPANE-TYPE TETRASUBSTITUTED ALKENES [J].
BRASE, S ;
DEMEIJERE, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (22) :2545-2547
[7]   Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones [J].
Burtin, G ;
Corringer, PJ ;
Hitchcock, PB ;
Young, DW .
TETRAHEDRON LETTERS, 1999, 40 (22) :4275-4278
[8]   Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids [J].
Burtin, G ;
Corringer, PJ ;
Young, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3451-3459
[9]   NEW PRENYLAMINE-ANALOGS - INVESTIGATIONS OF THEIR INFLUENCE ON CALCIUM-DEPENDENT BIOLOGICAL-SYSTEMS [J].
CALDIROLA, P ;
ZANDBERG, P ;
MANNHOLD, R ;
TIMMERMAN, H .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (7-8) :555-568
[10]  
Camacho DH, 1999, ANGEW CHEM INT EDIT, V38, P3365, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3365::AID-ANIE3365>3.0.CO