Total Synthesis of (−)-Bauhinin

The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Hor...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 84; no. 4; pp. 890 - 897
Main Authors Josien-Lefebvre, Delphine, Desmares, Guillaume, Drian, Claude Le
Format Journal Article
LanguageEnglish
Published Basel Verlag Helvetica Chimica Acta 18.04.2001
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACID
ABSOLUTE-CONFIGURATION
NAKED SUGARS
RESOLUTION
BIS-HYDROXYLATION
GLUCOSIDE
MEDICINAL-PLANTS
DERIVATIVES
CONSTITUENTS
DC
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Summary:The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra‐O‐isobutyryl‐D‐glucosyl bromide 9 as the reagent in the Koenigs‐Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (−)‐bauhinin (1).
Bibliography:ArticleID:HLCA890
istex:F6FDD05A30BAAFB3AF0F05230098C21AAAFC9CF6
ark:/67375/WNG-QCXC8ML2-V
ISSN:0018-019X
1522-2675
DOI:10.1002/1522-2675(20010418)84:4<890::AID-HLCA890>3.0.CO;2-Q