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
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
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页码:5843 / 5854
页数:12
相关论文
共 89 条
[21]   TUNICAMYCINS, STREPTOVIRUDINS, AND CORYNETOXINS, A SPECIAL SUBCLASS OF NUCLEOSIDE ANTIBIOTICS [J].
ECKARDT, K .
JOURNAL OF NATURAL PRODUCTS, 1983, 46 (04) :544-550
[22]   CORYNETOXINS, CAUSATIVE AGENTS OF ANNUAL RYEGRASS TOXICITY - THEIR IDENTIFICATION AS TUNICAMYCIN GROUP ANTIBIOTICS [J].
EDGAR, JA ;
FRAHN, JL ;
COCKRUM, PA ;
ANDERTON, N ;
JAGO, MV ;
CULVENOR, CCJ ;
JONES, AJ ;
MURRAY, K ;
SHAW, KJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (04) :222-224
[23]   TOTAL SYNTHESIS OF UNDECULOFURANOSIDURONIC ACID-DERIVATIVES RELATED TO HERBICIDINS [J].
EMERY, F ;
VOGEL, P .
TETRAHEDRON LETTERS, 1993, 34 (26) :4209-4212
[24]   STRUCTURAL IDENTITY OF ANTHELMYCIN WITH HIKIZIMYCIN [J].
ENNIFAR, S ;
DAS, BC ;
NASH, SM ;
NAGARAJAN, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (02) :41-42
[25]   NAKED SUGARS AS SYNTHETIC INTERMEDIATES .26. SYNTHESIS OF ALPHA-D-(1-]3) AND ALPHA-D-(1-]4)-C-LINKED GALACTOSIDES OF D-MANNOSE DERIVATIVES - CONFORMATION OF ALPHA-C-GALACTOSIDES [J].
FERRITTO, R ;
VOGEL, P .
TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2077-2092
[26]  
FREROT E, UNPUB
[27]  
GAGNAIRE D, 1963, B SOC CHIM FR, P2627
[28]  
GANEM B, 1978, J ORG CHEM, V43, P1607
[29]   HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF 2,5-ANHYDRO-3-DEOXY-D-HEXONIC AND 2,5-ANHYDRO-4-DEOXY-D-HEXONIC ACIDS AND OF THE RELATED DEOXYADENOSINES-C [J].
GASPARINI, F ;
VOGEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2451-2457
[30]   PREFERRED CONFORMATION OF C-GLYCOSIDES .7. PREFERRED CONFORMATION OF CARBON ANALOGS OF ISOMALTOSE AND GENTIOBIOSE [J].
GOEKJIAN, PG ;
WU, TC ;
KANG, HY ;
KISHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6422-6434