THE REACTION OF ALPHA-ALKOXYALLYLPHOSPHINE OXIDES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - AN APPROACH TO PROSTAGLANDIN PRECURSORS

被引:12
作者
BIRSE, EF [1 ]
IRONSIDE, MD [1 ]
MURRAY, AW [1 ]
机构
[1] UNIV DUNDEE,DEPT CHEM,DUNDEE DD1 4HN,SCOTLAND
关键词
D O I
10.1016/0040-4039(95)01218-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regiochemistry of the reaction of alpha-methoxyallylphosphine oxides with alpha, beta unsaturated carbonyl compounds has been studied. With 2-cyclopenten-1-ones, and using a transmetallation procedure, a nucleophilic beta-alkylation-electrophilic alpha-alkylation strategy which leads to advanced prostlgandin precursors has been developed.
引用
收藏
页码:6309 / 6312
页数:4
相关论文
共 17 条
[1]   STEREOCHEMICAL ASPECTS OF PROTON CHEMICAL-SHIFTS .3. CONFIGURATIONAL ASSIGNMENTS IN PENTACYCLIC SYSTEMS WITHOUT RECOURSE TO A KARPLUS EQUATION [J].
ANTEUNIS, M ;
DANNEELS, D .
ORGANIC MAGNETIC RESONANCE, 1975, 7 (07) :345-348
[2]   STEREOCHEMICAL AND MECHANISTIC ASPECTS OF THE APROTIC CONJUGATE ADDITION-REACTIONS OF THE CARBANIONS OF OCTENYL SULFIDES AND OCTENYL THIOCARBAMATES WITH 4-TERT-BUTOXYCYCLOPENT-2-ENONE IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE [J].
BINNS, MR ;
HAYNES, RK .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (05) :937-965
[3]   A ROUTE TO PROSTAGLANDIN PRECURSORS FROM 1-(PHENYLTHIO)-2-OCTENYLLITHIUM [J].
BINNS, MR ;
HAYNES, RK ;
LAMBERT, DE ;
SCHOBER, PA .
TETRAHEDRON LETTERS, 1985, 26 (28) :3385-3388
[4]   HMPA-MEDIATED CONJUGATE ADDITION OF ALKYLTHIOALLYL AND PHENYLTHIOALLYL ANIONS TO CYCLOPENTENONE [J].
BINNS, MR ;
HAYNES, RK ;
HOUSTON, TL ;
JACKSON, WR .
TETRAHEDRON LETTERS, 1980, 21 (06) :573-576
[5]   HEXAMETHYLPHOSPHORAMIDE-MEDIATED CONJUGATE ADDITION OF (ALKYLTHIO)ALLYLLITHIUM (PHENYLTHIO)ALLYLLITHIUM AND (PHENYLSELENO)ALLYLLITHIUM REAGENTS TO 2-CYCLOPENTENONE [J].
BINNS, MR ;
HAYNES, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3790-3795
[6]   THE DIASTEREOSPECIFIC APROTIC CONJUGATE ADDITION-REACTIONS OF ALLYLIC ANIONS - MECHANISTIC ASPECTS [J].
BINNS, MR ;
CHAI, OL ;
HAYNES, RK ;
KATSIFIS, AA ;
SCHOBER, PA ;
VONWILLER, SC .
TETRAHEDRON LETTERS, 1985, 26 (12) :1569-1572
[7]  
BIRSE EF, 1988, J CHEM RES M, P864
[8]  
BIRSE EF, 1989, J CHEM SOC P1, P1039
[9]  
DEVCHAND DK, 1986, TETRAHEDRON LETT, V27, P4635
[10]  
FETTES K, IN PRESS J CHEM SOC