STEREOSELECTIVE CONSTRUCTION OF THE COMPLETE INGENANE RING-SYSTEM

被引：38

作者：

FUNK, RL

OLMSTEAD, TA

PARVEZ, M

STALLMAN, JB

机构：

[1] Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, University Park

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 22期

关键词：

D O I：

10.1021/jo00074a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective route to the fully assembled and optically pure tetracyclic ring system of ingenol which features a macrocyclic Claisen rearrangement for the construction of the strained in,out-bridged bicyclic substructure and simultaneous, strategic placement of functionality has been developed.

引用

收藏

页码：5873 / 5875

页数：3

相关论文

共 35 条

[21] INGENANE SYNTHETIC STUDIES - AN EXPEDIENT APPROACH TO HIGHLY OXYGENATED ABC SUBUNITS OF INGENOL VIA REDUCTIVE DIALKYLATIVE ANNULATION AND ALPHA,BETA-EPOXY KETONE PHOTOISOMERIZATION [J].

PAQUETTE, LA ;

NITZ, TJ ;

ROSS, RJ ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (05) :1446-1454

[22] STEREOCONTROLLED CONSTRUCTION OF AN INGENOL PROTOTYPE HAVING A COMPLETE ARRAY OF OXYGENATED AND UNSATURATED CENTERS [J].

PAQUETTE, LA ;

ROSS, RJ ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6192-6204

[23] PROTEIN KINASE-C - A FAMILY AFFAIR [J].

PARKER, PJ ;

KOUR, G ;

MARAIS, RM ;

MITCHELL, F ;

PEARS, C ;

SCHAAP, D ;

STABEL, S ;

WEBSTER, C .

MOLECULAR AND CELLULAR ENDOCRINOLOGY, 1989, 65 (1-2) :1-11

[24] SYNTHETIC STUDIES ON INGENOL - BRIDGEHEAD ENOLATE REACTIVITY AND ABC RING ASSEMBLY [J].

RIGBY, JH ;

MOORE, TL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2959-2962

[25] INGENANE SYNTHETIC STUDIES - STEREOCONTROLLED INTRODUCTION OF ALL OXYGENATED AND UNSATURATED CENTERS IN AN INGENOL PROTOTYPE [J].

ROSS, RJ ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5497-5498

[26] ACTIVATION OF THE PKC-ISOTYPE-ALPHA, PKC-ISOTYPE-BETA-1, PKC-ISOTYPE-GAMMA, PKC-ISOTYPE-DELTA AND PKC-ISOTYPE-EPSILON BY PHORBOL ESTERS OF DIFFERENT BIOLOGICAL-ACTIVITIES [J].

RYVES, WJ ;

EVANS, AT ;

OLIVIER, AR ;

PARKER, PJ ;

EVANS, FJ .

FEBS LETTERS, 1991, 288 (1-2) :5-9

[27]

SATOH T, 1984, CHEM PHARM BULL, V32, P3452

[28]

SLAGA TJ, 1984, MECHANISM TUMOR PROM, V1

[29] CONFORMATIONALLY CONSTRAINED ANALOGS OF DIACYLGLYCEROL - INTERACTION OF GAMMA-LACTONES WITH THE PHORBOL ESTER RECEPTOR OF PROTEIN-KINASE-C [J].

TENG, K ;

MARQUEZ, VE ;

MILNE, GWA ;

BARCHI, JJ ;

KAZANIETZ, MG ;

LEWIN, NE ;

BLUMBERG, PM ;

ABUSHANAB, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :1059-1070

[30]

TRITTON TR, 1990, CANCER CELL-MON REV, V2, P95

← 1 2 3 4 →