ASYMMETRIC-SYNTHESIS OF 1-ALKYLTETRAHYDROISOQUINOLINES USING CHIRAL OXAZOLO[2,3-A]TETRAHYDROISOQUINOLINES

被引:69
作者
YAMATO, M
HASHIGAKI, K
QAIS, N
ISHIKAWA, S
机构
[1] Faculty of Pharmaceutical Sciences, University of Okayama, Okayama, 700
关键词
D O I
10.1016/S0040-4020(01)87916-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method of synthesizing enantiomerically pure (S)- and (R)-alkyl- and 1-aryltetrahydroisoquinolines has been achieved starting from isochroman with (R)- or (S)-phenylglycinol. © 1990.
引用
收藏
页码:5909 / 5920
页数:12
相关论文
共 13 条
[1]   THE CONSTITUENTS OF DYSOXYLUM-LENTICELLARE .1. PHENYLETHYLISOQUINOLINE, HOMOERYTHRINA, AND DIBENZAZECINE ALKALOIDS [J].
ALADESANMI, AJ ;
KELLEY, CJ ;
LEARY, JD .
JOURNAL OF NATURAL PRODUCTS, 1983, 46 (01) :127-131
[2]   CHEMICAL CORRELATION OF THE ABSOLUTE CONFIGURATIONS OF SALSOLIDINE, SALSOLINE, AND CALYCOTOMINE WITH THE AMINO-ACIDS [J].
BATTERSBY, AR ;
EDWARDS, TP .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1214-1221
[3]   SYNTHESIS AND ABSOLUTE CONFIGURATION OF CRYPTOSTYLINES I, II, AND III [J].
BROSSI, A ;
TEITEL, S .
HELVETICA CHIMICA ACTA, 1971, 54 (06) :1564-&
[4]  
HASHIGAKI K, 1988, SYNTHESIS-STUTTGART, P1001
[5]   INVESTIGATION ON DIASTEREOSELECTIVE C,C-BOND FORMATION IN THE 1-POSITION OF 1,2,3,4-TETRAHYDROISOQUINOLINES .2. EPC-SYNTHESIS OF TETRAHYDROISOQUINOLINES BY DIASTEREOSELECTIVE ALKYLATION AT THE 1-POSITION OF PHENYLALANINE-DERIVED PRECURSORS - SYNTHESIS OF THE ALKALOID (+)-CORLUMINE [J].
HUBER, IMP ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1987, 70 (07) :1944-1954
[6]   STUDIES ON ORCHIDACEAE ALKALOIDS .11. 3 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINES FROM CRYPTOSTYLIS FULVA SCHLTR [J].
LEANDER, K ;
LUNING, B ;
RUUSA, E .
ACTA CHEMICA SCANDINAVICA, 1969, 23 (01) :244-&
[7]   ASYMMETRIC-SYNTHESIS OF ISOQUINOLINE ALKALOIDS [J].
MEYERS, AI ;
DICKMAN, DA ;
BOES, M .
TETRAHEDRON, 1987, 43 (21) :5095-5108
[8]   ASYMMETRIC-SYNTHESIS OF ISOQUINOLINE ALKALOIDS BY HOMOGENEOUS CATALYSIS [J].
NOYORI, R ;
OHTA, M ;
HSIAO, Y ;
KITAMURA, M ;
OHTA, T ;
TAKAYA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7117-7119
[9]   STEREOSELECTIVE REDUCTIONS OF CHIRAL IMINIUM IONS [J].
POLNIASZEK, RP ;
MCKEE, JA .
TETRAHEDRON LETTERS, 1987, 28 (39) :4511-4514
[10]   UBER ISOCHROMAN .1. RINGOFFNUNG UND RINGSCHLUSS BEI ISOCHROMAN-ABKOMMLINGEN - ZWEI NEUE UMLAGERUNGEN [J].
RIECHE, A ;
SCHMITZ, E .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (05) :1254-1262