Total Synthesis of (2Z)-[(4R,5R,6S)-6-(β-D-Glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene]ethanenitrile, a Cyanoglucoside from Ilex warburgii

The total synthesis of the noncyanogenic cyanoglucoside 1, originally isolated from Ilex warburgii, was achieved in nine steps (9% overall yield), starting from an optically pure Diels–Alder adduct ((+)‐3). The key step of the synthesis, the glycosidation, was carried out under Koenigs–Knorr conditi...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 90; no. 1; pp. 19 - 30
Main Authors Josien-Lefebvre, Delphine, Le Drian, Claude
Format Journal Article
LanguageEnglish
Published Zürich WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cyano
Diels-Alder reactions
Glucoside
Glucoside, cyano
Glycosidation
Ilex warburgii
Koenigs-Knorr conditions
Naked sugars
Physical Sciences
Science & Technology
ENANTIOMERICALLY PURE
DERIVATIVES NAKED SUGARS
ABSOLUTE-CONFIGURATION
RESOLUTION
GLUCOSIDE
OPTICALLY PURE
GLYCOSYLATION
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Summary:The total synthesis of the noncyanogenic cyanoglucoside 1, originally isolated from Ilex warburgii, was achieved in nine steps (9% overall yield), starting from an optically pure Diels–Alder adduct ((+)‐3). The key step of the synthesis, the glycosidation, was carried out under Koenigs–Knorr conditions closely related to those developed for the total syntheses of (−)‐lithospermoside and (−)‐bauhinin. We had to tune the protecting groups used for the two free cis‐configured OH groups of the aglycone, which afforded the desired β‐d‐glucoside intermediate 15 in very good yield (62%).
Bibliography:ark:/67375/WNG-2CZDFBT6-7
istex:65B4E34D1250AAF1E747B7062AAF391EE4E8145C
ArticleID:HLCA200790015
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200790015