A new approach to the synthesis of (±)-methyl jasmonate and (±)-baclofen via conjugated addition of oxazoline cyanocuprate to Michael acceptors

Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture

“…Apart from naphthoquinone pigments, linoleic acid [ 17 ] and β-sitosterol [ 18 ] have been identified in both in vitro cultures. Additionally, methyl linolate [ 17 ] has been isolated from the cell suspension culture (also detected by GC-MS in the roots of other Boraginaceous species [ 19 , 20 ]) as well as methyl jasmonate ( 10 ) [ 21 , 22 ] (for the first time within the Boraginaceae family), a triglyceride mixture of palmitic, stearic and 8- Ζ - or 9- Ζ - or 11- Ζ or 9- Ε -octadecenoic acid (as determined after transesterification/methylation and GC-MS analysis of the resulting fatty acid methyl esters [ 23 ]) and also a mixture of 1-monoglycerides of palmitic, stearic and oleic acid (as determined after transesterification/methylation and GC-MS analysis of the resulting fatty acid methyl esters [ 23 ], as well as after GC-MS analysis of the silylated derivatives which were identified as 2,3- O -bis(trimethylsilyl)-1-glyceryl palmitate, stearate and oleate respectively) probably for the first time within Boraginaceae family.…”

Jasmonic acid biosynthesis by fungi: derivatives, first evidence on biochemical pathways and culture conditions for production

“…An interesting methodology leading only to racemic MeJA was proposed by Dos Santos et al (2001) based on the synthon equivalent to a carboxymethyl anion to enones and nitroalkenes, through a 1,4-addition reaction of 2,4,4-trimethyl-2-oxazoline cyanocuprate 3; afforded the (±)-MeJA in 32% overall yield from 2-cyclopenten-1-one.…”