ChemInform Abstract: NEW ROUTES FOR THE CONVERSION OF AUCUBIN TO 11‐DEOXY‐11‐METHYLPROSTAGLANDIN INTERMEDIATES

Abstract

Mit der Titelverbindung (I) als Ausgangsverbindung lassen sich über die Stufen von Monodesoxyaucubin (IIa) bzw. dessen Acetylderivat (IIb) die chiralen Bausteine (VI) bzw. (IX) synthetisieren.

Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

“…As expected, the 8α-epimer 23 was predominant when Pt was used (α:β ratio 10:1), while Pd/C catalysis in this case only afforded an α:β ratio of 1:3 (i.e., between 23 and 24 ). The 13 C NMR signals for C-9 and C-10 were more lowfield in 8β-epimer 24 as compared to 8α-epimer 23 , in accordance with data for related iridoid epimers …”

Efficient Conversion of Aucubin into 6-epi-Aucubin

“…Iridoids represent a large group of natural monoterpenoids, which can be advantageously used as starting material for the chiral pool synthesis of various bioactive compounds. − For instance, the synthesis of chiral prostanoids from iridoid glycosides is well documented. − Aucubin ( 1 ) is often used as starting material in these syntheses, because it can be readily extracted in large amounts from the fruits or leaves of Aucuba japonica Thunb . (Cornaceae).…”

Chiral Synthons from the Iridoid Glucoside Antirrhinoside − Synthesis of a Carbocyclic Homonucleoside Analogue

“…On the contrary, we succeeded in protecting the allylic hydroxyl functions by employing methyl chloroformate in pyridine and dichloromethane under DMPA catalysis (Scheme 4). We obtained the expected dicarbonate (18) together with the tricarbonate derivative (17). The allylic hydroxyls proved to be more reactive than the primary hydroxyl under these conditions.…”