Reductive aromatization of quinols:: Synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin

被引:45
作者
Parker, KA [1 ]
Georges, AT [1 ]
机构
[1] Brown Univ, Dept Chem, Providence, RI 02912 USA
关键词
D O I
10.1021/ol991346l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment with mCPBA afforded the tricyclic papulacandin framework. Alternatively, hydroboration gave the chaetiacandin nucleus.
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页码:497 / 499
页数:3
相关论文
共 32 条
[1]   Quinone alkylation using organocadmium reagents: A general synthesis of quinols [J].
Aponick, A ;
McKinley, JD ;
Raber, JC ;
Wigal, CT .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2676-2678
[2]   PAPULACANDIN-B - INHIBITOR OF GLUCAN SYNTHESIS IN YEAST SPHEROPLASTS [J].
BAGULEY, BC ;
ROMMELE, G ;
GRUNER, J ;
WEHRLI, W .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1979, 97 (02) :345-351
[3]   Total synthesis and structural elucidation of the antifungal agent papulacandin D [J].
Barrett, AGM ;
Pena, M ;
Willardsen, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1082-1100
[4]   TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT PAPULACANDIN-D [J].
BARRETT, AGM ;
PENA, M ;
WILLARDSEN, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) :1147-1148
[5]   APPROACHES TOWARDS THE SYNTHESIS OF PAPULACANDIN-D - PREPARATION AND STRUCTURAL ELUCIDATION OF THE ACYL SIDE-CHAIN [J].
BARRETT, AGM ;
PENA, M ;
WILLARDSEN, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) :1145-1146
[6]   C-GLYCOSIDES .9. STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDIC SPIROKETAL OF THE PAPULACANDINS [J].
CZERNECKI, S ;
PERLAT, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6289-6292
[7]   A FULLY SYNTHETIC ROUTE TO THE PAPULACANDINS - STEREOSPECIFIC SPIROACETALIZATION OF A C-1-ARYLATED METHYL GLYCOSIDE [J].
DANISHEFSKY, S ;
PHILLIPS, G ;
CIUFOLINI, M .
CARBOHYDRATE RESEARCH, 1987, 171 :317-327
[8]   ANTIBIOTICS THAT INHIBIT FUNGAL CELL-WALL DEVELOPMENT [J].
DEBONO, M ;
GORDEE, RS .
ANNUAL REVIEW OF MICROBIOLOGY, 1994, 48 :471-497
[9]   ARYLATION OF 1-TRIBUTYLSTANNYL GLYCALS CATALYZED BY PALLADIUM - A SYNTHETIC ROUTE TO THE BASIC SKELETON OF THE PAPULACANDINS AND CHAETIACANDIN [J].
DUBOIS, E ;
BEAU, JM .
TETRAHEDRON LETTERS, 1990, 31 (36) :5165-5168
[10]  
DUBOIS E, 1992, CARBOHYDR RES, V223