Indium-mediated highly diastereoselective allenylation in aqueous medium: total synthesis of (+)-goniofufurone

被引：58

作者：

Yi, XH ^{[1
]}

Meng, Y ^{[1
]}

Li, CJ ^{[1
]}

机构：

[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 04期

关键词：

D O I：

10.1039/a707881a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(+)-Goniofufurone was synthesized from D-glucurono-6,3-lactone via an indium-mediated highly regio- and diastereo-selective allenylation of carbonyl compounds in aqueous medium.

引用

页码：449 / 450

页数：2

共 18 条

[1] NOVEL BIOACTIVE STYRYL-LACTONES - GONIOFUFURONE, GONIOPYPYRONE, AND 8-ACETYLGONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) - X-RAY MOLECULAR-STRUCTURE OF GONIOFUFURONE AND OF GONIOPYPYRONE [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

FANWICK, PE ;

MCLAUGHLIN, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1655-1661

[2] 2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

MCLAUGHLIN, JL ;

FANWICK, PE .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1034-1043

[3] INDIUM-MEDIATED COUPLING OF ALDEHYDES WITH PROP-2-YNYL BROMIDES IN AQUEOUS-MEDIA [J].

ISAAC, MB ;

CHAN, TH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1003-1004

[4] TIN-MEDIATED AND INDIUM-MEDIATED ALLYLATION IN AQUEOUS-MEDIA - APPLICATION TO UNPROTECTED CARBOHYDRATES [J].

KIM, E ;

GORDON, DM ;

SCHMID, W ;

WHITESIDES, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5500-5507

[5] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications [J].

Li, CJ .

TETRAHEDRON, 1996, 52 (16) :5643-5668

[6] AN OPTICALLY-ACTIVE CHROMIUM(0)-COMPLEXED BENZALDEHYDE DERIVATIVE IN ORGANIC-SYNTHESIS - A HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-GONIOFUFURONE [J].

MUKAI, C ;

KIM, IJ ;

HANAOKA, M .

TETRAHEDRON LETTERS, 1993, 34 (38) :6081-6082

[7] THE TOTAL SYNTHESIS OF GONIOFUFURONE [J].

MURPHY, PJ ;

DENNISON, ST .

TETRAHEDRON, 1993, 49 (30) :6695-6700

[8] Addition of allylindium reagents to aldehydes substituted at C-alpha or C-beta with heteroatomic functional groups. Analysis of the modulation in diastereoselectivity attainable in aqueous, organic, and mixed solvent systems [J].

Paquette, LA ;

Mitzel, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :1931-1937

[9] THE SYNTHESIS OF CHLORODEOXYHEXOFURANOID DERIVATIVES [J].

PAROLIS, H .

CARBOHYDRATE RESEARCH, 1983, 114 (01) :21-33

[10] ETHOXYCARBONYLMETHYLENETRIPHENYLPHOSPHORANE IN CARBOHYDRATE-CHEMISTRY .2. A SHORT AND EFFICIENT SYNTHESIS OF (+)-GONIOFUFURONE [J].

PRAKASH, KRC ;

RAO, SP .

TETRAHEDRON, 1993, 49 (07) :1505-1510

← 1 2 →