Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Heating the 16- E-oxime of isosteviol ( ent-16- E-hydroxyiminobeyeran-19-oic acid) with concentrated hydrochloric acid (or 25% H 2SO 4) at 110 °C leads to the formation of lactone of 4α-carboxy-13α-hydroxy-13,16-seco- ent-19-norbeyeran-16-oic acid as the main product, whereas approximately equal qua...

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Veröffentlicht in:Mendeleev communications 2005, Vol.15 (1), p.27-29
Hauptverfasser: Militsina, Olesya I., Kovyljaeva, Galina I., Bakaleynik, Galina A., Strobykina, Irina Yu, Kataev, Vladimir E., Alfonsov, Vladimir A., Musin, Rashid Z., Beskrovny, Dmitry V., Litvinov, Igor A.
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Sprache:eng
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Zusammenfassung:Heating the 16- E-oxime of isosteviol ( ent-16- E-hydroxyiminobeyeran-19-oic acid) with concentrated hydrochloric acid (or 25% H 2SO 4) at 110 °C leads to the formation of lactone of 4α-carboxy-13α-hydroxy-13,16-seco- ent-19-norbeyeran-16-oic acid as the main product, whereas approximately equal quantities of this lactone and lactam of 4α-carboxy-13α-amino-13,16-seco- ent-19-norbeyeran-16-oic acid are formed by heating the 16- E-oxime of isosteviol with concentrated hydrochloric acid in an ampoule at 180 °C.
ISSN:0959-9436
DOI:10.1070/MC2005v015n01ABEH001946