C-ARYL GLYCOSIDES - ELECTROPHILE INITIATED CYCLIZATIONS OF 6-ARYL-5-HEXEN-2-OLS

被引：33

作者：

HART, DJ

LEROY, V

MERRIMAN, GH

YOUNG, DGJ

机构：

[1] Department of Chemistry, Ohio State University, Columbus, Ohio 43210

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 21期

关键词：

D O I：

10.1021/jo00047a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

引用

页码：5670 / 5680

页数：11

共 74 条

[1] PALLADIUM-CATALYZED REACTIONS OF GLYCALS WITH (1,3-DIMETHYL-2,4(1H,3H)-PYRIMIDINEDION-5-YL)MERCURIC ACETATE - FACILE REGIOSPECIFIC AND STEREOSPECIFIC C-NUCLEOSIDE SYNTHESES [J].