PRACTICAL PREPARATION OF ALPHA-HYDROXY-BETA-AMINO ESTER UNITS STEREOSELECTIVE SYNTHESIS OF TAXOL SIDE-CHAIN AND NORSTATINE

被引：67

作者：

HATTORI, K ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)86992-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric reaction of chiral imines with alpha-silyloxy ketene acetals mediated by chiral boron reagents is described. The key to its success is the use of the chiral boron complex prepared in situ form (R)- or (S)-binaphthol and B(OPh)(3). Both diastereomers of alpha-hydroxy-beta-amino ester units are successfully prepared with high selectivities by the chiral boron reagents depending on the geometry of the silyl ketene acetals. The optically pure anti alpha-hydroxy-beta-amino ester is obtained from (E)-silyl ketene acetal, while the corresponding syn alpha-hydroxy-beta-amino ester is obtained from (2)-silyl ketene acetal. The method can be efficiently applied to the stereoselective synthesis of taxol C-13 side chain and the norstatine family.

引用

页码：2785 / 2792

页数：8

共 21 条

[11]

KOBAYASHI Y, 1991, CHEM PHARM BULL, V39, P2550

[12] A STEREOSELECTIVE SYNTHESIS OF THE (2R,3S)-3-AMINO-2-HYDROXYBUTYRIC AND (2S,3R)-3-AMINO-2-HYDROXYBUTYRIC ACID-DERIVATIVES, THE KEY COMPONENTS OF A RENIN INHIBITOR AND BESTATIN [J].

KOBAYASHI, Y ;

TAKEMOTO, Y ;

KAMIJO, T ;

HARADA, H ;

ITO, Y ;

TERASHIMA, S .

TETRAHEDRON, 1992, 48 (10) :1853-1868

[13]

KOIKE H, 1989, GENDAI KAGAKU, P55

[14] APPLICATION OF THE VICINAL OXYAMINATION REACTION WITH ASYMMETRIC INDUCTION TO THE HEMISYNTHESIS OF TAXOL AND ANALOGS [J].

MANGATAL, L ;

ADELINE, MT ;

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

POTIER, P .

TETRAHEDRON, 1989, 45 (13) :4177-4190

[15] SYNTHESIS AND EVALUATION OF SOME WATER-SOLUBLE PRODRUGS AND DERIVATIVES OF TAXOL WITH ANTITUMOR-ACTIVITY [J].

MATHEW, AE ;

MEJILLANO, MR ;

NATH, JP ;

HIMES, RH ;

STELLA, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) :145-151

[16] A BRIEF SURVEY OF TAXUS ALKALOIDS AND OTHER TAXANE DERIVATIVES [J].

MILLER, RW .

JOURNAL OF NATURAL PRODUCTS, 1980, 43 (04) :425-437

[17]

OJIMA L, 1992, TETRAHEDRON LETT, V39, P5737

[18]

OJIMA L, 1992, TETRAHEDRON, V34, P6985

[19] PEPSTATIN-DERIVED INHIBITORS OF ASPARTIC PROTEINASES - A CLOSE LOOK AT AN APPARENT TRANSITION-STATE ANALOG INHIBITOR [J].

RICH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (03) :263-273

[20] BIOLOGICALLY-ACTIVE TAXOL ANALOGS WITH DELETED A-RING SIDE-CHAIN SUBSTITUENTS AND VARIABLE C-2' CONFIGURATIONS [J].

SWINDELL, CS ;

KRAUSS, NE ;

HORWITZ, SB ;

RINGEL, I .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1176-1184

← 1 2 3 →