this bee has been fantasizing about a dream that goes from vanillin >> mmda for quite a while, however there is one big stumbling block. Nitroethane. (can't get it and a monumental pain to synth it)
wracking my brain for an alternative route to hearts desire, it has occured to me that eugenol is the allybenzene equivalent of vanillin. so here is what i propose,
eugenol >>
bromine in MeOH >> 3methoxy,4hydroxy, 5bromo allybenzene >>
NaOH >> hydroxyeugenol ( 3methoxy,4,5hydroxy allybenzene) >> >> methelenation via
DCM, NaOH, DMSO >> 3methoxy,4,5methlenedioxy allybenzene (looks alot like myristicin, hmm?)
this allybenzene can then be isomerized to the propenylbenzene, run through a pseudonitrosite synth to yeild the nitropropene and reduced by a multitude of methods to the beolved amino derivative.
unfortunately the most questionable step is the 1st. i am unsure whether the bromination technique outlined by Os and Rhod in the MMDA synth will bromintate the 5 position in the ring or whether it will brominate the beta carbon on the tail. if it does want to go to the beta carbon, any suggestions how to inhibit this allowing dominant bromination at the 5 position?
more than one way to skin a cat(maybe) feel free to point out any other shortcomings above.
is it soup yet?