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EP0078686A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for making gibberellins

Assignee: Australian National University
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Filing: 1982-10-29
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Granted: —
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Expires: 2002-10-29
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Abstract

Abstract The invention provides a process for the preparation of 1,2-dihydro-2-hydroxy gibberellin acids of the general formula (10): <CHEM> therein R<2> is H, OH, alkoxy, substituted alkoxy or acyloxy, and R<3> and R<4>, are each H or alkyl, from precursor gibberellin acids of formula (11): <CHEM> and/or formula 13 <CHEM> by reaction with a compound of general formula (12) M<-> (R<6>)3 BH<-> 12 wherein M<-> represents a monovalent cation and R<6> represents an alkyl group, in the presence of a proton source when a compound of formula (11) is used. This process 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 acid.

Inventors

  • 👤 John Vincent Turner
  • 👤 Russell Arthur Bell

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-01 18:12
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 140 words
A process for the preparation of a compound of the general formula (10): wherein R 2 is H, OH, alkoxy, substituted alkoxy, or acyloxy; and R 3 and R 4 are each H or alkyl; characterised in that a Δ(1)-3-keto gibberellin of the general formula (11): wherein R 2 , R 3 and R 4 are as hereinbefore defined or a 3-keto gibberellin of the general formula (13): wherein R 2 , R and R 4 are as hereinbefore defined or a mixture of 3-keto gibberellins of the general formulae (11) and (13) is reacted with a compound of the general formula (12): wherein M + represents a monovalent cation and R 6 represents an alkyl group,in the presence also of a proton source where a compound of formula (11) is to be converted into a compound of formula (10).
Claim 2
Dependent Claim 140 words
A process for the preparation of a compound of the general formula (10): wherein R 2 is H, OH, alkoxy, substituted alkoxy, or acyloxy; and R 3 and R 4 are each H or alkyl; characterised in that a Δ(1)-3-keto gibberellin of the general formula (11): wherein R 2 , R 3 and R 4 are as hereinbefore defined or a 3-keto gibberellin of the general formula (13): wherein R 2 , R and R 4 are as hereinbefore defined or a mixture of 3-keto gibberellins of the general formulae (11) and (13) is reacted with a compound of the general formula (12): wherein M + represents a monovalent cation and R 6 represents an alkyl group,in the presence also of a proton source where a compound of formula (11) is to be converted into a compound of formula (10).
Claim 3
Dependent Claim 22 words
A process as claimed in claim 1 wherein the compound of general formula (12) is lithium tri-sec-butylborohydride, potassium tri-sec-butylborohydride or potassium triethylborohydride.
Claim 4
Dependent Claim 43 words
A process as claimed in claim 1 for the preparation of a compound of the general formula (lOa): wherein the radicals R 2 R and R are as defined in claim 1, wherein the compound of general formula (12) used is potassium tri-sec-butylborohydride.
Claim 5
Dependent Claim 22 words
A process as claimed in any of claims 1 to 3 wherein the proton source is an alkanol or a hydrogenphosphate salt.
Claim 6
Dependent Claim 19 words
A process as claimed in claim 4 wherein the hydrogenphosphate salt is potassium dihydrogenphosphate, sodium dihydrogenphosphate or dipotassium hydrogenphosphate.
Claim 7
Dependent Claim 37 words
A process as claimed in any of claims 1 to 5 wherein the radicals R 3 and R 4 are each H, methyl or ethyl; and wherein R 2 is H, OH, methoxy, methoxymethoxy, acetoxy, or dichloroacetoxy.
Claim 8
Dependent Claim 20 words
A process as claimed in claim 6 wherein the radicals R 2 , R and R 4 all represent H.
Claim 9
Dependent Claim 25 words
A process as claimed in claim 6 wherein the radicals R 3 and R 4 both represent H and the radical R 2 represents OH.

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