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Neighbouring group participation on the bromination of methyl gibberellate: X-ray molecular structure of methyl 3,13-di-O-acetylgibberellate 16β,17-dibromide and ent-3α,13-diacetoxy-17-bromo-10β,16β-dihydroxy-20-norgibberell-1-ene-7,19-dioic acid 19,10-lactone 7-methyl ester

AuthorsCollado, Isidro G.; Fraga, Braulio M. ; Hanson, James R.; Hitchcock, Peter B.; García-Tellado, Fernando
Issue Date1988
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions I 1988(1): 105-110 (1988)
AbstractBromination of methyl gibberellate at C-16 with trimethyl(phenyl)ammonium perbromide has been shown to be non-stereospecific. However only the (16R)-epimer readily rearranged to the 8,13-epigibberellin. The stereochemistry of the (16S)-epimer was established by X-ray analysis. Bromination of methyl diacetylgibberellate afforded a (16R)-hydroxy-17-bromide. Bromination under strictly anhydrous conditions led to the isomerization of ring A to the Δ1-19,2-lactones. Reaction with bromine in the presence of sodium hydrogen carbonate also gave a 1β,2α-dibromo adduct.
Description6 pages, 2 figures, 5 tables.
Appears in Collections:(IPNA) Artículos
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