Diastereoselective synthesis of polysubstituted pyrrolidinone as a key intermediate for the anticancer agents by palladium(II)-catalyzed carboxylation

被引:19
作者
Choi, DR [1 ]
Lee, KY [1 ]
Chung, YS [1 ]
Joo, JE [1 ]
Kim, YH [1 ]
Oh, CY [1 ]
Lee, YS [1 ]
Ham, WH [1 ]
机构
[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea
关键词
palladium; carboxylation; pyrrolidinone; stereocontrol;
D O I
10.1007/BF02977706
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Palladium(II)-catalyzed carboxylation of chiral olefins 6a-d has been examined under various conditions. In the weak basic condition (K2CO3), 7a-d were obtained in good yields. Alternatively, in the strong basic condition, pyrrolidinones 8a-d were obtained resulting in excellent yields and with high diastereoselectivity.
引用
收藏
页码:151 / 158
页数:8
相关论文
共 19 条
[1]   Synthesis of optically pure highly functionalized γ-lactams via 2-azetidinone-tethered iminophosphoranes [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :993-996
[2]   Azaspirene:: A novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartotya sp. [J].
Asami, Y ;
Kakeya, H ;
Onose, R ;
Yoshida, A ;
Matsuzaki, H ;
Osada, H .
ORGANIC LETTERS, 2002, 4 (17) :2845-2848
[3]   ALLENIC AMINO-ACIDS .1. SYNTHESIS OF GAMMA-ALLENIC GABA BY A NOVEL AZA-COPE REARRANGEMENT [J].
CASTELHANO, AL ;
KRANTZ, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1877-1879
[4]   A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity [J].
Corey, EJ ;
Li, WD ;
Reichard, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2330-2336
[5]   Salinosporamide A:: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora [J].
Feling, RH ;
Buchanan, GO ;
Mincer, TJ ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) :355-+
[6]  
HARRISON T, 1995, CONTEMP ORG SYNTH, P209
[7]   Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor [J].
Hayashi, Y ;
Shoji, M ;
Yamaguchi, J ;
Sato, K ;
Yamaguchi, S ;
Mukaiyama, T ;
Sakai, K ;
Asami, Y ;
Kakeya, H ;
Osada, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12078-12079
[8]   A flexible approach to (S)-5-alkyl tetramic acid derivatives:: Application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA [J].
Huang, PQ ;
Wu, TJ ;
Ruan, YP .
ORGANIC LETTERS, 2003, 5 (23) :4341-4344
[9]   Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0) [J].
Lee, KY ;
Kim, YH ;
Park, MS ;
Oh, CY ;
Ham, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9450-9458
[10]   Stereoselective alkylations in rigid systems.: Effect of remote substituents on π-facial additions to lactam enolates.: Stereoelectronic and steric effects [J].
Meyers, AI ;
Seefeld, MA ;
Lefker, BA ;
Blake, JF ;
Williard, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7429-7438