SYNTHESIS OF UNDECULOFURANOSIDE DERIVATIVES OF THE HERBICIDINS AND OF ANALOGS

被引：34

作者：

EMERY, F ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,BCH DORIGNY,CHIM SECT,CH-1015 LAUSANNE,SWITZERLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 18期

关键词：

D O I：

10.1021/jo00123a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.

引用

页码：5843 / 5854

页数：12

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