SYNTHESIS OF (-)-EGENINE (DECUMBENSINE) BY ASYMMETRIC CARBONYL ADDITION

被引:23
作者
REIN, KS [1 ]
GAWLEY, RE [1 ]
机构
[1] UNIV MIAMI,DEPT CHEM,CORAL GABLES,FL 33124
关键词
D O I
10.1016/S0040-4039(00)97451-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of the phthalideisoquinoline hemiacetal egenine is reported, along with spectral data suggesting that egenine and decumbensine are one and the same. These synthetic studies are part of a larger investigation into the face-selectivity of additions of chiral dipole-stabilized organometallics to aldehydes. The synthesis of egenine and the correlation to bicuculline diol establish the absolute configuration of the major stereoisomer formed as being opposite to that expected based on earlier work. © 1990.
引用
收藏
页码:3711 / 3714
页数:4
相关论文
共 10 条
[1]   ON THE RELATIVE ENERGIES OF ABINITIO STRUCTURES OF N-METHYLFORMAMIDE ANIONS AND THEIR LITHIUM DERIVATIVES - AN ESTIMATE OF THE MAGNITUDE OF CHELATE STABILIZATION [J].
BARTOLOTTI, LJ ;
GAWLEY, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2980-2982
[2]   ACYCLIC STEREOSELECTION IN THE ALKYLATION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS - A SELF-IMMOLATIVE CHIRALITY TRANSFER PROCESS FOR THE SYNTHESIS OF PRIMARY AMINES [J].
GAWLEY, RE ;
REIN, K ;
CHEMBURKAR, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3002-3004
[3]   SYNTHESIS OF R-LAUDANOSINE AND 9-R-O-METHYLFLAVINANTINE BY ASYMMETRIC ALKYLATION [J].
GAWLEY, RE ;
SMITH, GA .
TETRAHEDRON LETTERS, 1988, 29 (03) :301-302
[4]   EGENINE - A POSSIBLE INTERMEDIATE IN PHTHALIDEISOQUINOLINE BIOGENESIS [J].
GOZLER, B ;
GOZLER, T ;
SHAMMA, M .
TETRAHEDRON, 1983, 39 (04) :577-580
[5]  
MCPHAIL A, COMMUNICATION
[6]   CHROMATOGRAPHIC-SEPARATION OF THE ENANTIOMERS OF N-ACYLATED HETEROCYCLIC AMINES [J].
PIRKLE, WH ;
WELCH, CJ ;
MAHLER, GS ;
MEYERS, AI ;
FUENTES, LM ;
BOES, M .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) :2504-2506
[7]   (+)-DECUMBENSINE AND (+)-EPI-ALPHA-DECUMBENSINE ARE NOT ALPHA-HYDROXYBENZYLTETRAHYDROISOQUINOLINES [J].
ROZWADOWSKA, MD ;
MATECKA, D ;
BROZDA, D .
TETRAHEDRON LETTERS, 1989, 30 (45) :6215-6218
[8]   ON THE STERIC COURSE OF ADDITION OF 1-LITHO-2-PIVALOYL-1,2,3,4-TETRAHYDROISOQUINOLINE AND 1-MAGNESIO-2-PIVALOYL-1,2,3,4-TETRAHYDROISOQUINOLINE TO ALDEHYDES AND KETONES - AN X-RAY CRYSTAL-STRUCTURE DETERMINATION OF THE ORGANOMAGNESIUM REAGENT [J].
SEEBACH, D ;
HANSEN, J ;
SEILER, P ;
GROMEK, JM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :1-13
[9]  
WU TS, 1988, HETEROCYCLES, V27, P1565
[10]   DECUMBENSINE AND EPI-ALPHA-DECUMBENSINE - 2 NEW ALKALOIDS ISOLATED FROM CORYDALIS-DECUMBENS [J].
ZHANG, JS ;
XU, RS ;
QUIRION, JC .
JOURNAL OF NATURAL PRODUCTS, 1988, 51 (06) :1241-1242