Naturalproductman’s Blog

Hey, is that a natural product?!

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.

racemic

OL paper

About these ads

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.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s

 
Follow

Get every new post delivered to your Inbox.

Join 69 other followers

%d bloggers like this: