ACID-CATALYZED REARRANGEMENT OF TREVOAGENIN-A AND TREVOAGENIN-B - THE ACETAL FUNCTION AS ELECTRON-DONOR GROUP IN HETEROLYTIC FRAGMENTATIONS

Simple item page
dc.contributor.authorFRANCISCO, CG
dc.contributor.authorFREIRE, R
dc.contributor.authorHERNANDEZ, R
dc.contributor.authorSALAZAR, JA
dc.contributor.authorSUAREZ, E
dc.contributor.authorCORTES, M
dc.date.accessioned2025-01-23T19:44:01Z
dc.date.available2025-01-23T19:44:01Z
dc.date.issued1983
dc.description.abstractThe acid-catalyzed rearrangement of trevoagenins A (1) and B (4) [constituents of Trevoa trinervis] gave 3.beta.-hydroxy-24-oxo-16,17-sec-5.alpha.-dammar-17(20)E-ene-16,30-lactone (5) (40%), its 17(20)Z-ene isomer (7) (13%), and (20R,24R)-3.beta.,25-dihydroxy-15.alpha.,30-cyclo-20,24-epoxy-5.alpha.-dammaran-16-one (9) (2%). Compounds (5) and (7) were produced through a heterolytic fragmentation mechanism. In order to study the scope of this rearrangement the C-20 epimeric hydroxy acetals (24) and (28) were synthesized starting from trevoagenin B and A, respectively. The reaction of the 20S-hydroxy acetal (24) with I led to the Z-olefin (29) while the 20R-hydroxy acetal (28) gave the E-olefin (30). The concerted nature of this heterolytic fragmentation, where acetals or hemiacetals are the electron-donor groups, is supported by the observed stereospecificity of the reaction.
dc.fuente.origenWOS
dc.identifier.issn1472-7781
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/99913
dc.identifier.wosidWOS:A1983RR20700029
dc.issue.numero11
dc.language.isoen
dc.pagina.final2763
dc.pagina.inicio2757
dc.revistaJournal of the chemical society-perkin transactions 1
dc.rightsacceso restringido
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleACID-CATALYZED REARRANGEMENT OF TREVOAGENIN-A AND TREVOAGENIN-B - THE ACETAL FUNCTION AS ELECTRON-DONOR GROUP IN HETEROLYTIC FRAGMENTATIONS
dc.typeartículo
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
Files
Collections
Artículos de revistas