Process for making gibberellins

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D30794

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045323348

ABSTRACT:
Processes for the preparation of 1,2-dihydro-3-hydroxy gibberellin acids of general formula (1) from precursor gibberellin acids that employs conditions which (a) do not require prior protection of the free carboxylic acid group; (b) preserve the .DELTA.(16)-olefinic bond and the lactone; and (c) enable the stereochemistry of the hydroxyl moiety at position 3 to be controlled, enabling access to the individual stereoisomers of the 1,2-dihydro-3-hydroxy gibberellin acids; said processes comprising the reaction of either a 3-keto gibberellin of general formula (2), or of the general formula (3), or a mixture thereof, in the presence or absence of a proton source depending on the particular precursor gibberellin acid, with a compound of general formula (4):

REFERENCES:
patent: 4241221 (1980-12-01), Grudzinskas et al.
Murofushi et al., Chem. Abs. 88: 7093h.

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