Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

LN Mander, JV Turner and BG Coombe

Australian Journal of Chemistry 27(9) 1985 - 2000
Published: 1974

Abstract

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).

https://doi.org/10.1071/CH9741985

© CSIRO 1974

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions