TOTAL SYNTHESIS OF SIMMONDSIN

被引：23

作者：

CHIDA, N ^{[1
]}

YAMADA, K ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV, FAC SCI & TECHNOL, DEPT APPL CHEM, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 08期

关键词：

D O I：

10.1039/c39910000588

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the naturally occurring cyanoglucoside, simmondsin 1, starting from L-quebrachitol and D-glucose, is described, revealing the absolute configuration of this compound.

引用

页码：588 / 590

页数：3

共 14 条

[1] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

TAKECHI, N ;

OZAKI, S .

TETRAHEDRON LETTERS, 1990, 31 (10) :1433-1434

[2] TOTAL SYNTHESIS OF BENGAMIDE-E [J].

CHIDA, N ;

TOBE, T ;

OGAWA, S .

TETRAHEDRON LETTERS, 1991, 32 (08) :1063-1066

[3] A FORMAL TOTAL SYNTHESIS OF (-)-ISOAVENACIOLIDE FROM L-QUEBRACHITOL [J].

CHIDA, N ;

TOBE, T ;

SUWAMA, M ;

OHTSUKA, M ;

OGAWA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) :994-995

[4] A SIMPLE ROUTE TO BETA,BETA-TREHALOSE VIA TRICHLOROACETIMIDATES [J].

COOK, SJ ;

KHAN, R ;

BROWN, JM .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1984, 3 (02) :343-348

[5]

DWUMABADU D, 1976, LLOYDIA, V39, P385

[6] STRUCTURE AND STEREOCHEMISTRY OF SIMMONDSIN [J].

ELLIGER, CA ;

WAISS, AC ;

LUNDIN, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) :2930-2931

[7] SIMMONDSIN, AN UNUSUAL 2-CYANOMETHYLENECYCLOHEXYL GLUCOSIDE FROM SIMMONDSIA-CALIFORNICA [J].

ELLIGER, CA ;

WAISS, AC ;

LUNDIN, RE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (19) :2209-2212

[8] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

HORITA, K ;

YOSHIOKA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1986, 42 (11) :3021-3028

[9] EFFICIENT SYNTHETIC ROUTES TO FLUORINATED ISOSTERES OF INOSITOL AND THEIR EFFECTS ON CELLULAR GROWTH [J].

KOZIKOWSKI, AP ;

FAUQ, AH ;

POWIS, G ;

MELDER, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4528-4531

[10] PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS [J].

MIYASHITA, M ;

YOSHIKOSHI, A ;

GRIECO, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3772-3774

← 1 2 →