ENANTIOSPECIFIC SYNTHESIS OF POLYHYDROXY AMINO-ACIDS - SYNTHESIS OF THE C33-C38 PORTION OF CALYCULINS

被引：37

作者：

KOSKINEN, AMP

CHEN, JS

机构：

[1] Department of Chemistry, University of Surrey Guildford

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 47期

关键词：

CALYCULIN; ENANTIOSPECIFIC SYNTHESIS; POLYHYDROXY AMINO ACIDS; CIS-HYDROXYLATION;

D O I：

10.1016/0040-4039(91)80459-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of 2,3-dihydroxy-4-dimethylamino-5-methoxypentanoic acid, the C33-C37 portion of the antibiotic calyculin has been achieved.

引用

页码：6977 / 6980

页数：4

共 20 条

[1] ENANTIOSPECIFIC SYNTHESIS OF D-ALPHA,OMEGA-DIAMINOALKANOIC ACIDS [J].

BEAULIEU, PL ;

SCHILLER, PW .

TETRAHEDRON LETTERS, 1988, 29 (17) :2019-2022

[2] NEW METHOD FOR METHYLATION OF AMINES [J].

BORCH, RF ;

HASSID, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) :1673-&

[3] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[4] OKADAIC ACID - A NEW PROBE FOR THE STUDY OF CELLULAR-REGULATION [J].

COHEN, P ;

HOLMES, CFB ;

TSUKITANI, Y .

TRENDS IN BIOCHEMICAL SCIENCES, 1990, 15 (03) :98-102

[5] REVERSAL OF ALDEHYDE DIASTEREOFACIAL SELECTIVITY IN A METHYL KETONE ALDOL REACTION - APPLICATION TO THE SYNTHESIS OF THE CALYCULIN SPIROKETAL [J].

EVANS, DA ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (43) :6129-6132

[6] CODON-61 MUTATIONS IN THE C-HARVEY-RAS GENE IN MOUSE SKIN TUMORS INDUCED BY 7,12-DIMETHYLBENZ[A]ANTHRACENE PLUS OKADAIC ACID CLASS TUMOR PROMOTERS [J].

FUJIKI, H ;

SUGANUMA, M ;

YOSHIZAWA, S ;

KANAZAWA, H ;

SUGIMURA, T ;

MANAM, S ;

KAHN, SM ;

JIANG, W ;

HOSHINA, S ;

WEINSTEIN, IB .

MOLECULAR CARCINOGENESIS, 1989, 2 (04) :184-187

[7] GLYCOSYL ALPHA-AMINO-ACIDS VIA STEREOCONTROLLED BUILDUP OF A PENALDIC ACID EQUIVALENT - A NOVEL SYNTHETIC APPROACH TO THE NUCLEOSIDIC COMPONENT OF THE POLYOXINS AND RELATED SUBSTANCES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3772-3787

[8] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[9]

GRIBBLE GW, 1987, SYNTHESIS-STUTTGART, P709

[10] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS [J].

HOFFMANN, RW .

CHEMICAL REVIEWS, 1989, 89 (08) :1841-1860

← 1 2 →