Regioselective reduction of N-alkyl-3-sulfonyl-glutarimide.: Formal synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen

被引:0
作者
Chang, MY
Chen, ST [1 ]
Chang, NC
机构
[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 80424, Taiwan
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of N-alkyl-3-sulfonylglutarimides with (1) sodium hydride and then with lithium aluminum hydride, or (2) sodium borohydride yielded two different types of regioselectively reduced hydroxypiperidinones which were further dehydrated to two pyridin-2-ones in the presence of boron trifluoride etherate. Cycloaddition and regioselective reduction were combined to synthesize 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen.
引用
收藏
页码:99 / 112
页数:14
相关论文
共 49 条
[1]  
AKIMOTO H, 1974, CHEM PHARM BULL, V22, P2614
[2]   Michael addition of nitromethane to non-racemic chiral Cr(CO)3 complexes of ethyl cinnamate derivatives:: stereoselective synthesis of (R)-(-)-baclofen [J].
Baldoli, C ;
Maiorana, S ;
Licandro, E ;
Perdicchia, D ;
Vandoni, B .
TETRAHEDRON-ASYMMETRY, 2000, 11 (09) :2007-2014
[3]   THE USE OF TRIPHENYLPHOSPHINE DIETHYL AZODICARBOXYLATE (DEAD) FOR THE CYCLIZATION OF 1,4-AMINO AND 1,5-AMINO ALCOHOLS [J].
BERNOTAS, RC ;
CUBE, RV .
TETRAHEDRON LETTERS, 1991, 32 (02) :161-164
[4]  
BOWERY NE, 1982, TRENDS PHARMACOL SCI, V31, P400
[5]   Heck arylations of N-acyl-3-pyrroline and N-acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts.: Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues [J].
Carpes, MJS ;
Correia, CRD .
TETRAHEDRON LETTERS, 2002, 43 (05) :741-744
[6]   Enantioselective synthesis of (-)-indolizidine 167B [J].
Chalard, P ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC ;
Canet, I .
TETRAHEDRON LETTERS, 1999, 40 (09) :1661-1664
[7]   Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)-lasubine II and (+)-subcosine II [J].
Chalard, P ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC .
TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4361-4368
[8]   New synthesis of 3-aryl-N-n-propyl-piperidines [J].
Chang, MY ;
Chen, ST ;
Chang, NC .
TETRAHEDRON, 2002, 58 (18) :3623-3628
[9]   An efficient synthesis of N-benzyl-3-sulfonyl glutarimides.: Formal synthesis of the aromatase inhibitor AG-1 [J].
Chang, MY ;
Chang, BR ;
Tai, HM ;
Chang, NC .
TETRAHEDRON LETTERS, 2000, 41 (52) :10273-10276
[10]   Enzyme catalysed oxidation of nazlinin and nazlinin derivatives. Characterisation of the reaction products. [J].
Cheng, E ;
Botzem, J ;
Wanner, MJ ;
Burm, BEA ;
Koomen, GJ .
TETRAHEDRON, 1996, 52 (19) :6725-6732