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
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.
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页码:7019 / 7032
页数:14
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