ChemInform Abstract: SYNTHETIC PLANT GROWTH REGULATORS. VI. THE PARTIAL SYNTHESIS OF OPTICALLY ACTIVE (4β,15α)-18-NORKAURENE-15-CARBOXYLIC ACIDS FROM (4β)-18-NORKAUREN-3-ONE BY MEANS OF A PYRROLIDINIUM YLIDE REARRANGEMENT

1981 ◽  
Vol 12 (1) ◽  
Author(s):  
A. L. COSSEY ◽  
L. N. MANDER ◽  
J. V. TURNER
Keyword(s):  
Plant Growth ◽  
Carboxylic Acids ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Optically Active ◽  
Partial Synthesis

Synthetic plant growth regulators. VI. The partial synthesis of optically active (4β,15α)-18-Norkaurene-15-carboxylic acids from (4β)-18-norkauren-3-one by means of a pyrrolidinium ylide rearrangement

1980 ◽  
Vol 33 (9) ◽  
pp. 2061 ◽  
Author(s):  
AL Cossey ◽  
LN Mander ◽  
JV Turner
Keyword(s):  
Carboxylic Acid ◽  
Plant Growth ◽  
Carboxylic Acids ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Sodium Borohydride ◽  
Sigmatropic Rearrangement ◽  
Optically Active ◽  
Allylic Amines ◽  
Partial Synthesis

(4β)-18-Norkaur-16-en-3-one (4a) was alternatively acetalized (ethanediol/Dowex resin) or deoxygenated (tosylhydrazine/sodium borohydride); allylic bromination (N-bromosuccinimide) of the products, followed by alkylation of pyrrolidine gave primary allylic amines which were quaternized with chloroacetonitrile. Potassium t-butoxide-induced [2,3]-sigmatropic rearrangement, followed by acidic hydrolysis and Jones oxidation, gave respectively (4β,15α)-3-oxo-18-norkaur-16-ene-15- carboxylic acid (10a) and (4β,15α)-18-norkaur-16-ene-15-carboxylic acid. Reductions of (4a) and (10a) gave, with K-Selectride, axial (3β)- alcohols and, with sodium borohydride, mainly equatorial (3α)-alcohols. Details of a related conversion of (+)-phyllocladene into (15α)- phyllocladene-15-carboxylic acid are also recorded.

Synthesis of optically active cyclohexanone analogs of the plant hormone abscisic acid

1990 ◽  
Vol 68 (7) ◽  
pp. 1151-1162 ◽  
Author(s):  
Nancy Lamb ◽  
Suzanne R. Abrams
Keyword(s):  
Abscisic Acid ◽  
Plant Growth ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Plant Hormone ◽  
Optically Active ◽  
Common Precursor

The abscisic acid analogs (−)-(4R,5R)-, (+)-(4S,5S)-, and (−)-(4S,5R)-4(1E,3Z)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3,3,5-trimethylcyclohexanones (dihydroabscisic acids), and (−)-(4S,5R)-, (+)-(4R,5S)-, and (−)-(4R,5R)-4(Z)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanones were synthesized from a common precursor, (−)-(6R)-2,2,6-trimethylcyclohexan-1,4-dione, which was readily prepared by the fermentation of oxoisophorone with bakers' yeast. Keywords: abscisic acid, dihydroabscisic acid, acetylenic analogs, optically active analogs, plant growth regulators.

Wheat regenerants in the system of rapid assessment of the effect of 24-epibrassinolide

Biomics ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 394-397
Author(s):  
Seldimirova O.A. ◽  
M.V. Bezrukova ◽  
N.N. Кruglova ◽  
F.М. Shakirova
Keyword(s):  
Plant Growth ◽  
Experimental Model ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Drought Resistance ◽  
Rapid Assessment ◽  
Immature Embryo ◽  
Model System ◽  
Wheat Cultivars ◽  
Experimental Model System

The influence of 24-epibrassinolide on the efficiency of regenerants obtained from embryonic calli formation was studied in wheat cultivars contrast for drought resistance. The possibility of using the experimental model system «immature embryo – embryonic callus – regenerant» in the rapid assessment of the effect of antistress plant growth regulators is shown.

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