Semisynthesis of abrusoside A methyl ester

被引：9

作者：

Kim, NC

Kinghorn, AD

Kim, DSHL ^{[1
]}

机构：

[1] Univ Illinois, Coll Pharm, Program Collaborat Res Pharmaceut Sci, Chicago, IL 60612 USA

[2] Univ Illinois, Coll Pharm, Dept Med Chem & Pharmacognosy, Chicago, IL 60612 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol9905598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Abrusoside A methyl ester (6) was prepared from abrusogenin (1) through methylation (CH2N2) and a subsequent coupling reaction with 1-chloro-2,3,4,6-tetra-O-acetylglucopyranose (3) in the presence of AgOTf and TMU in CH2Cl2, followed by deacetylation using K2CO3 in MeOH-H2O.

引用

收藏

页码：223 / 224

页数：2

相关论文

共 8 条

[1] A ROUTE TO ARTIFICIAL GLYCOCONJUGATES AND OLIGOSACCHARIDES VIA ENZYMATICALLY RESOLVED GLYCALS - DRAMATIC EFFECTS OF THE HANDEDNESS OF THE SUGAR DOMAIN UPON THE PROPERTIES OF AN ANTHRACYCLINE DRUG [J].

BERKOWITZ, DB ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4518-4529

[2] ABRUSOSIDE A - A NEW TYPE OF HIGHLY SWEET TRITERPENE GLYCOSIDE [J].

CHOI, YH ;

KINGHORN, AD ;

SHI, XB ;

ZHANG, H ;

TEO, BK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :887-888

[3] POTENTIAL SWEETENING AGENTS OF PLANT-ORIGIN .21. ABRUSOSIDES-A-D, 4 NOVEL SWEET-TASTING TRITERPENE GLYCOSIDES FROM THE LEAVES OF ABRUS-PRECATORIUS [J].

CHOI, YH ;

HUSSAIN, RA ;

PEZZUTO, JM ;

KINGHORN, AD ;

MORTON, JF .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05) :1118-1127

[4] APPLICATION OF GLYCALS TO THE SYNTHESIS OF OLIGOSACCHARIDES - CONVERGENT TOTAL SYNTHESES OF THE LEWIS-X TRISACCHARIDE SIALYL-LEWIS-X ANTIGENIC DETERMINANT AND HIGHER CONGENERS [J].

DANISHEFSKY, SJ ;

GERVAY, J ;

PETERSON, JM ;

MCDONALD, FE ;

KOSEKI, K ;

GRIFFITH, DA ;

ORIYAMA, T ;

MARSDEN, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1940-1953

[5] Abrusoside E, a further sweet-tasting cycloartane glycoside from the leaves of Abrus precatorius [J].

Kennelly, EJ ;

Cai, LN ;

Kim, NC ;

Kinghorn, AD .

PHYTOCHEMISTRY, 1996, 41 (05) :1381-1383

[6] A DIRECT ROUTE FROM 1-ALPHA,2-ALPHA-ANHYDROGLUCOSE DERIVATIVES TO ALPHA-GLUCOSIDES [J].

LIU, KKC ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1895-1897

[7] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[8] SYNTHESES OF SWEET TASTING DITERPENE GLYCOSIDES, BAIYUNOSIDE AND ANALOGS [J].

YAMADA, H ;

NISHIZAWA, M .

TETRAHEDRON, 1992, 48 (15) :3021-3044