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Synlett 1991; 1991(7): 526-528
DOI: 10.1055/s-1991-20788
DOI: 10.1055/s-1991-20788
letter
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The Intramolecular Diels-Alder Reaction with Furan-Diene: A Novel Route to (±)-Gibberellin A5
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Publication History
Publication Date:
07 March 2002 (online)
A novel potential approach to 20-norgibberellins is described and exemplified with the total synthesis of (±)-gibberellin A5 from methyl (1S,2R, 5S)-2-(2-furyl)-5-hydroxy-6-methylenebicyclo[3.2.1]octane-1-carboxylate. Key steps involve an intramolecular Diels-Alder reaction with the furan-diene moiety leading to a kaurenoid analogue and the subsequent ring contraction of the central 5-membered ring to yield the required carboxy-substituted cyclopentane moiety via a photochemical α-diazo ketone Wolff rearrangement.