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Acid-catalysed rearrangement of trevoagenins A and B. The acetal function as electron-donor group in heterolytic fragmentations

AuthorsFrancisco, Cosme G. ; Freire, Raimundo ; Hernández, Rosendo ; Salazar, José A.; Suárez, Ernesto ; Cortés, Manuel
Issue Date1983
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions 1983: 2757-2763 (1983)
AbstractThe acid-catalysed rearrangement of trevoagenins A (1) and B (4) gave 3-hydroxy-24-oxo-16,17-seco-5-dammar-17(20)E-eno-16,30-lactone (5)(40%), its 17(20)Z-ene isomer (7)(13%), and (20R,24R)-3,25-dihydroxy-15,30-cyclo-20,24-epoxy-5-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 iodine 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.
Description7 pages, 1 figure, 1 table, 1 scheme.
Publisher version (URL)http://dx.doi.org/10.1039/P19830002757
Appears in Collections:(IPNA) Artículos
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