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Articles tagged with: oxidative-cyclisation

Still In The RBF »

[7 Aug 2010 | 15 Comments | 19,891 views]
Cortistatins A (J, K and L) Pt. IV

Myers, Flyer, Si. Nat. Chem., 2010, AOP. DOI: 10.1038/nchem.794
Cortistatin is one of those targets like platensimycin that has attracted an almost unhealthy synthetic lust in the last few years, with three previous appearances in these interwebs (Baran, Nicolaou, Shair).  The reasons for both are the same – both have remarkable biological profiles, and both are of challenging complexity.  However, both are now what I’d call mature targets – in that the best disconnections have been tried, and that there are unavoidable methods that feature in most routes.  However, that …

Still In The RBF »

[25 Jan 2009 | 37 Comments | 14,342 views]
Helicterin B, Helisorin, and Helisterculin A

Snyder and Kontes. JACS, 2009, ASAP. DOI: 10.1021/ja806865u.
It’s amazing how ideas arrive in pairs. Think: Deep Impact and Armageddon, or The Prestige and The Illusionist. Or bloody Peter Mandelson and Ken Clarke… And in as many weeks, we have Porco’s synthesis of chamaecypanone C and Synder’s synthesis of helicterin B, united through the key use of a retro-Diels-Alder/Diels-Alder cascade. The ‘why?’ in this case seems to be a shared love of dimeric (and tetrameric) natural products, where this kind of chemistry is a …

Still In The RBF »

[19 Jan 2009 | 20 Comments | 8,326 views]
Chamaecypanone C

Porco, Dong, Hamel, Bai, Covell, and Beutler. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200804883.
It’s not often I’m surprised by the origin of natural products, afterall ocean trenches, acidic pits and frozen wastelands have all revealed ‘tartan TLC-plates’, but I didn’t consider tree heartwoods as likely targets. On second thought, why not? Loads of trees yield interesting isolates, but there’s something about heartwood that makes me think ‘woody’, and not much else… I mean, I’m currently resting my forearms on a lump of beech – and I’ve never …