SYNTHESIS OF ENANTIOMERIC PURE INTERMEDIATE FOR THE LACTONE PORTION OF COMPACTIN AND MEVINOLIN

被引:16
作者
CARDANI, S [1 ]
SCOLASTICO, C [1 ]
VILLA, R [1 ]
机构
[1] UNIV MILAN,CNR,CTR SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
关键词
D O I
10.1016/S0040-4020(01)87907-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diastereo and enantioselective synthesis of compound 11 a potential useful intermediate for the lactone portion of mevinolin and compactin was developed. Our strategy is based on the high stereoselective Michael addition of alkoxide to chiral norephedrine-derived oxazolidine 4. © 1990.
引用
收藏
页码:7283 / 7288
页数:6
相关论文
共 14 条
[1]   MEVINOLIN - A HIGHLY POTENT COMPETITIVE INHIBITOR OF HYDROXYMETHYLGLUTARYL-COENZYME-A REDUCTASE AND A CHOLESTEROL-LOWERING AGENT [J].
ALBERTS, AW ;
CHEN, J ;
KURON, G ;
HUNT, V ;
HUFF, J ;
HOFFMAN, C ;
ROTHROCK, J ;
LOPEZ, M ;
JOSHUA, H ;
HARRIS, E ;
PATCHETT, A ;
MONAGHAN, R ;
CURRIE, S ;
STAPLEY, E ;
ALBERSSCHONBERG, G ;
HENSENS, O ;
HIRSHFIELD, J ;
HOOGSTEEN, K ;
LIESCH, J ;
SPRINGER, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (07) :3957-3961
[2]   NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION [J].
BERNARDI, A ;
CARDANI, S ;
PILATI, T ;
POLI, G ;
SCOLASTICO, C ;
VILLA, R .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1600-1607
[3]   ALLYLIC STEREOCENTER DIRECTED CYCLOPROPANATION - A NEW HIGHLY ENANTIOSELECTIVE SYNTHESIS OF HEMICARONIC ALDEHYDE [J].
BERNARDI, A ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3733-3734
[4]  
BERNARDI A, 1988, TETRAHEDRON, V44, P5563
[5]  
BERNARDI A, 1986, J ORG CHEM, V51, P5042
[6]  
BERNARDI A, IN PRESS TETRAHEDRON
[7]   ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION OF CUPRATES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE - ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-4-BENZYLOXYBUTANAL AND 2-ALKYL-4-OXOPENTANAL [J].
CARDANI, S ;
POLI, G ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON, 1988, 44 (18) :5929-5938
[8]  
CARDANI S, 1989, TETRAHEDRON, V45, P7404
[9]  
CHEN K, 1987, TETRAHEDRON LETT, P155