Synthetic Plant Growth Regulators. IV. The Preparation of Hydroxylated Helminthosporic Acid Analogues

1979 ◽  
Vol 32 (4) ◽  
pp. 823 ◽  
Author(s):  
LN Mander ◽  
LT Palmer
Keyword(s):  
Plant Growth ◽  
Plant Growth Regulators ◽  
Lewis Acid ◽  
Growth Regulators ◽  
Sodium Borohydride ◽  
Sigmatropic Rearrangement ◽  
Hydroxyl Group ◽  
Hydroxy Ketone ◽  
Wittig Olefination ◽  
Sequential Reduction

Sequential reduction (sodium borohydride, metal-ammonia, hydrogenation) of ketone (8) gave the hydroxy ketone (9) which was converted into olefin (10) (Wittig olefination) and thence to acid (14) by means of the [2,3] sigmatropic rearrangement of ylide (12) to (13). Acid (15) was similarly prepared from alcohol (11) which was obtained by deoxygenation of ketone (9). The tetrahydrocuminic acid (16) was hydroxylated (lithium diisopropylamine, oxygen); the new hydroxyl group was protected with a dichloroacetyl function and then converted into the diazoketone. Lewis-acid-induced cyclization of (17) gave the bicyclooctanone (18a) plus its Δ3-isomer (18b), both of which were reduced and hydrolysed to hydroxy ketone (19). Wittig methylenation of (19) gave olefin (20) which was rearranged by acid to ketone (21). Both (20) and (21) were elaborated further to the acids (6) and (25), respectively, by the procedures used in the preparation of acids (14) and (15).

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.

Synthetic plant growth regulators. I. The synthesis of (±)-14-Norhelminthosporic acid and related compounds

1974 ◽  
Vol 27 (9) ◽  
pp. 1985 ◽  
Author(s):  
LN Mander ◽  
JV Turner ◽  
BG Coombe
Keyword(s):  
Plant Growth ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Sigmatropic Rearrangement ◽  
Ammonium Bromide ◽  
Reductive Methylation ◽  
Allylic Bromide ◽  
Related Compounds

Cuminic acid (9) was converted by reductive methylation into 1,2,3,6-tetrahydro-4-isopropyl-1- methylbenzoic acid (12). Acid-catalysed cyclization of the diazomethyl ketone (8) derived from (12), followed by hydrogenation, gave the bicyclo[3,2,l]octanone derivative (7), which was then converted through the allylic bromide mixture of (18) and (19) into the p-toluenesulphonyldithiocarbazone (21) and the allylic ammonium bromide (25). The [2,3]-sigmatropic rearrangement of the dithio- carbene derived from (21) and the ylid derived from (25) afforded the dithioester (22) and pyrrolidine (26), respectively, from which the alcohol (24), aldehydes (27) and (28), and acids (5) and (6) were prepared. Bioassay of (5), (6), (27) and (28) indicated gibberellin-like properties for all these compounds with potency comparable with that of helminthosporic acid (2).

Plant growth regulators in Eucalyptus grandis. IV. Synthetic approaches to G-regulator analogues

1982 ◽  
Vol 35 (7) ◽  
pp. 1411 ◽  
Author(s):  
ML Bolte ◽  
WD Crow ◽  
S Yoshida
Keyword(s):  
Plant Growth ◽  
Plant Growth Regulators ◽  
Lewis Acid ◽  
Growth Regulators ◽  
Good Yield ◽  
Acid Catalysis ◽  
Physiological Activity ◽  
Eucalyptus Grandis ◽  
Synthetic Approach ◽  
Synthetic Approaches

A new synthetic approach is described to the plant growth regulators of the hexahydrobenzo[e]- 1,2-dioxin group (the G-regulators of Eucalyptus grandis). Condensation of 1,3-diketones with aldehydes under Lewis acid catalysis gives, in good yield, the 1 : 2 adducts (4H-1,3-dioxins); these are simultaneously cleaved and (with some exceptions) oxidized on silica gel to the desired structure. In this way synthesis of a number of G-regulator analogues of similar physiological activity has been achieved.

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.

Somatic Embryogenesis and Plant Development in Eight Cultivars of Pecan

HortScience ◽  
1990 ◽  
Vol 25 (5) ◽  
pp. 573-576 ◽  
Author(s):  
I.E. Yates ◽  
C.C. Reilly
Keyword(s):  
Somatic Embryogenesis ◽  
Plant Growth ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Plant Development ◽  
Fruit Development ◽  
Somatic Embryos ◽  
Carya Illinoensis ◽  
Appreciable Variation

The influence of stage of fruit development and plant growth regulators on somatic embryogenesis and the relation of cultivar response on somatic embryogenesis and subsequent plant development have been investigated in eight cultivars of pecan [Carya illinoensis (Wangenh.) C. Koch]. Explants from the micropylar region of the ovule were more embryogenic when removed from fruits in the liquid endosperm stage than were intact ovules from less-mature fruits or from cotyledonary segments of more-mature fruits. Explants conditioned on medium containing auxin alone or auxin + cytokinin produced more somatic embryos than medium containing cytokinin alone. Under the conditions of this study, frequency of embryogenesis, as well as the germination of somatic embryos leading to plant development, indicated appreciable variation among cultivars. Plant development was greatest by far from somatic embryos of `Schley' than other cultivars studied.

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