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- W2023253503 abstract "Umsetzung des “trans”-p-Toluolsulfonates 9b mit Natrium-methylsulfinylmethid in Dimethylsulfoxid führte neben Kondensationsprodukten zum δ,ϵ-ungesättigten Aldehyd 12a. Die baseninduzierte Reaktion des “cis”-p-Toluolsulfonates 10b ergab dagegen durch intramolekulare Susbtitution ausschließlich das Oxetan 13. In analoger Weise reagierte das Hydroxyloganin-Derivate 16c zum Oxetan 18, während das 6-Epihydroxyloganin-Derivat 15c mit 67% Ausbeute zum Secologanin-aglyconmethyläther (1b) gespalten werden konnte. In Abhängigkeit von den Reaktionsbedingungen wurde hierbei als zweites Produkt das Secologaninsäure-Derivat 20a gebildet, das sich mit Natriumborhydrid zur Hydroxycarbonsäure 24 reduzieren und durch anschließende Destillation in den Swerosid-aglyconmethyläther 2b überführen ließ. Die Reduktion von 1b führe direkt zu 2b. Iridoide, V Biogenetic Type Synthesis of Secologanin- and Sweroside Aglycone O-Methyl Ether Reaction of the “trans”-p-toluenesulfonate 9b with sodium methylsulfinylmethide in dimethyl sulfoxide gave the δ,ϵ-unsaturated aldehyde 12a besides polymeric products. On the other hand treatement of the “cis”-p--toluenesulfonate 10b with base yielded by intramolecular nucleophilic substitution only an oxetane 13. According to this the hydroxyloganin derivative 16c led to the oxetane 18, whereas the 6-epihydroxyloganin derivative 15c could be cleaved to secologanin-aglycone O-methyl ether 1b. Depending on the reaction-conditions the secologanic acid compound 20a was formed as a byproduct. 20a could be reduced to the hydroxy acid 24, which was converted to sweroside aglycone O-methyl ether 2b by distillation. Reduction of 1b led directly to 2b." @default.
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- W2023253503 date "1976-11-01" @default.
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- W2023253503 title "Iridoide, V Biogeneseähnliche Synthese von Secologanin‐ und Swerosid‐aglyconmethyläther" @default.
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- W2023253503 doi "https://doi.org/10.1002/cber.19761091116" @default.
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