| Abstrakt: |
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%). [ABSTRACT FROM AUTHOR] |
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