A partial synthesis of gibberellin A14-aldehyde, a probable biosynthetic intermediate of gibberellins.
β Scribed by P. Hedden; J. MacMillan
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 98 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We have recently shcun' that gibberellin Al*-aldehyde (I), a central intermediate in gibberellin biosynthesis, 2,3 is efficiently converted into gibberellin A l4 (V) by cultures of Gibberella fujikuroi, thus providing direct evidence for the suggestion3 that 3-hydroxylation
π SIMILAR VOLUMES
SINCE the total syntheaia of (f)-glbberlc1\*2 and (\*I-epigibberic2 acids had been accompllshed , our efforts were directed to the synthesis of gibbane compounda containing the lha-lactone bridge which is characteristic to all gibbere111ns. We now rlsh to describe a partial synthesis of gibberellln
In our previous studies on gibberellin synthesis we have described a general approach to the construction of the ring A lactone system as present in gibberellins such as Gibberellic acid and Gibberellin A4 (l), based on the reductive alkylation of a P-methoxybenzoic acid 192 . We have also described
The epimeric gibberellin-A 7-aldehydes 1 and 2 were silylated, enolised with KH and 3labelled with -3 H20 to give after desilylation the tritium-labelled epimeric gibberellin-A ?-aldehydes 2 and 2. Subsequent acetylation, oxidation and deacetylation afforded [ 6-3H] gibberellin-A3 (6) and [ 6-3H]6-e