Abstract

Photoceyclization of diacetylgibberellin-A3-7-aldehyde 1 leads to the epimeric hydroxycyclobutanes 2 and 3. The configurations at the new asymmetric centres at C-7 and C-15 of the four-membered ring have been determined by 1H-NMR (homonuclear decoupling and INDOR techniques). Retroaldol-like cleavage of 2 and 3 under mild alkaline conditions gives the starting aldehyde 1 and the Δ 15 -isomeric aldehyde 6. Oxidation and deacetylation of 6 afford 16,17-dihydro-15,16-dehydro-gibberellin-A 3 7.

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