Synthesis of Vinyl-Containing Lupane- and a-Secolupane-Type Triterpene Esters

Synthesis of Vinyl-Containing Lupane- and a-Secolupane-Type Triterpene Esters

Vinyl-containing lupane- and oleanane-type C-3 and C-28 esters were synthesized from betulin and A-secotriterpene alcohols. The reaction of 2,3-secolupane alcohol 5 with vinylacetic acid produced ester 8 and a recyclization product, methyl 2β,3β-dihydroxylup-20(29)-en-28-oate ( 13 ), which was forme...

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Veröffentlicht in:Chemistry of natural compounds 2016-03, Vol.52 (2), p.256-261
Hauptverfasser: Krainova, G. F., Tolmacheva, I. A., El’tsov, O. S., Gorbunova, M. N., Grishko, V. V.
Format: Artikel
Sprache:eng
Schlagworte:
Esters
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
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Zusammenfassung:Vinyl-containing lupane- and oleanane-type C-3 and C-28 esters were synthesized from betulin and A-secotriterpene alcohols. The reaction of 2,3-secolupane alcohol 5 with vinylacetic acid produced ester 8 and a recyclization product, methyl 2β,3β-dihydroxylup-20(29)-en-28-oate ( 13 ), which was formed quantitatively in the reaction of 5 with maleic acid.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-016-1608-5