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The partial synthesis of beyergibberellin A4 and A9 methyl esters

AuthorsFraga, Braulio M. ; González, Antonio G.; Hernández, Melchor G.; Duri, Zvitendo J.; Hanson, James R.
Issue Date1984
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions I 1984: 1105-1107 (1984)
AbstractBeyergibberellins A4 and A9 methyl esters were synthesized from methyl gibberellate via gibberellin A1 methyl ester and its 3-epimer. The C/D ring junction of the 3-epimer was isomerized to afford the 16-oxo-8,13-isogibberellin and 3-hydroxy group removed by tributyltin hydride reduction of the corresponding chloride. Alternatively the C/D ring junction of the gibberellin A1 methyl ester was isomerized and the 3-hydroxy group was converted into its trimethylsilylethoxymethyl derivative. Reduction of the 16-ketones and elimination of the corresponding 16-sulphonate esters over alumina or with collidine afforded the title compounds.
Description3 pages, 5 schemes.-- Part of this work has appeared in a preliminary communication: Fraga, B.M. et al, "The chemical and microbiological synthesis of beyergibberellin A9", Tetrahedron Letters 24(18): 1945-1948 (1983).
Publisher version (URL)http://dx.doi.org/10.1039/P19840001105
Appears in Collections:(IPNA) Artículos
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