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The stereochemistry of a rearrangement and fragmentation reaction of ring D of 13-hydroxygibberellins

AuthorsCollado, Isidro G.; Fraga, Braulio M. ; Hanson, James R.; Hitchcock, Peter B.; García-Tellado, Fernando
Aqueous solution
Potassium Carbonates
Chemical rearrangement
Substituent effect
Crystalline structure
Experimental study
X ray diffraction
Molecular structure
Issue Date1988
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions I 1988(6): 1451-1454 (1988)
AbstractTreatment of methyl 16(R)- and 16(S)-16,17-dibromo-16,17-dihydrogibberellate with aqueous potassium carbonate at room temperature affords an 8,13-epigibberellin from the 16(R)-epimer whilst the 16(S)-epimer reacts much more slowly to give a 16-bromo-13,16,17-fused oxetane and a 16-bromo-13,16-secogibberellin, indicating the importance of the stereochemistry of the 16-substituent in determining the reaction pathway.
Description4 pages, 1 figure, 2 tables, 1 scheme.-- Supporting information available: Tables of bond lengths, bond and torsion angles, and temperature factors have been deposited at the Cambridge Crystallographic Data Centre.
Publisher version (URL)http://dx.doi.org/10.1039/P19880001451
Appears in Collections:(IPNA) Artículos
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