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Gibberellins 89. synthesis of gibberellin a 55 and gibberellin a 57 as well as 1 oxygenated gibberellin a 5 and gibberellin a 20 analogs a new principle for the regioselective transposition of an allylic alcohol function



Gibberellins 89. synthesis of gibberellin a 55 and gibberellin a 57 as well as 1 oxygenated gibberellin a 5 and gibberellin a 20 analogs a new principle for the regioselective transposition of an allylic alcohol function



Tetrahedron 39(3): 449-454



The synthesis of a series of 1-oxygenated gibberellins starting from GA3 is described. Nucleophilic addition of hydrazoic acid to 3-dehydro GA3 was followed by NaBH4 reduction of the resulting 1-azido-3-ketones 4 and 5 to the corresponding azido alcohols 8-10, and photolysis of the latter compounds to instable 1-imines which were smoothly hydrolyzed to the 1-oxo-3-hydroxy gibberelins 13 and 14. Subsequent NaBH4 reduction led to GA57 and GA55 and their 3-epimers, 17 and 18, respectively. In further steps 1-oxo-GA5, 1.alpha.- and 1.beta.-hydroxy-GA5 1-oxo-GA20 as well as 1.alpha.- and 1.beta.-hydroxy-GA20 were available. The structures of the synthesized gibberellins were determined by physical data, in regard to the stereochemistry at C-1 and C-3 especially on the basis of 1H NMR and ORD [optical rotary dispersion] measurements.

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