Syntheses through cascade dimerization
Posted by naturalproductman on August 30, 2012
Andrew Lawrence and co-workers at Australian National University have reported in Organic Letters on the syntheses of some polycyclic natural products, incarviditone and incarvilleatone.
OL paper
Like this:
Like Loading...
Related
This entry was posted on August 30, 2012 at 5:30 am and is filed under Dimer, Methodology, Total Synthesis.
You can follow any responses to this entry through the RSS 2.0 feed.
You can leave a response, or trackback from your own site.
milkshake said
examples of masterful biomimetic synthetic design like this one bring back the excitement I once felt about total synthesis. Please note that if the monomeric spiro intermediate could be made or resolved in optically pure form , only the desired (revised) compound would form without the isomer
naturalproductman said
Right – in other words if the monomeric rengyolone (compound 2 in the paper, although I don’t think this has a spirocyclic center) can be synthesized asymmetrically through maybe an intramolecular asymmetric oxy-Michal addition, the final dimerized product would be one enantiomer. I guess the challenge is to be able to synthesize rengyolone enantioselectively. I don’t know if this matters: but I think compounds can crystallize better when they are racemic.