scholarly journals Studies on Plant-Growth Regulators. IV. Structure of Growth Retardants and Syntheses of Related Compounds

1970 ◽  
Vol 18 (2) ◽  
pp. 243-248 ◽  
Author(s):  
TOSHIHIKO OKAMOTO ◽  
YO ISOGAI ◽  
TORU KOIZUMI ◽  
TAKENORI NISHINO ◽  
YAEKO SATOH
Keyword(s):  
Plant Growth ◽  
Plant Growth Regulators ◽  
Growth Regulators ◽  
Growth Retardants ◽  
Related Compounds

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).

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