Naturalproductman’s Blog

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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

2 Responses to “Syntheses through cascade dimerization”

  1. 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.

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