TOTAL, ASYMMETRIC-SYNTHESIS OF DEOXYPOLYOXIN-C

被引：61

作者：

AUBERSON, Y ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,2 RUE BARRE,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 20期

关键词：

D O I：

10.1016/S0040-4020(01)87887-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting with the Diels-Alder adduct 16 of furan to 1-cyanovinyl (1S')-camphanate deoxypolyoxin C (4) has been obtained in 11 steps and 4.8 % overall yield with recovery of the chiral auxiliary ((1S)-camphanic acid) at an early stage of the synthesis. The method implies bromination of(-)-2-(tert-butyl) dimethylsilyl]oxy-5-exo6-exo-(isopropylidenedioxy)-7-oxabicyclo[2.2.1]hept-2-ene(-)-12) and its highly stereoselective transformation into (-)-benzyl (l23-O-triacetyl-5-azido-5-deoxy-ga- and β-D-allofuranosid)-uronate (9). Procedures for the stereoselective substitution of C(3) in S-exo6-exo-(isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((+-)-11) by nitrogen containing moieties are also presented. © 1990.

引用

页码：7019 / 7032

页数：14

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