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Articles Archive for August 2011

Featured, Still In The RBF »

[20 Aug 2011 | 28 Comments | 12,790 views]
Axinellamines Pt. II

Baran, Su, Rodriguez. J. Am. Chem. Soc, 2011, ASAP. DOI: 10.1021/ja206191g
When does a person or groups work in a particular area of total synthesis become pedestrian, or even dull? This may sound harsh (especially as he’s a really nice guy), but Paterson’s (at Cambridge) work on macrolides isn’t doing it for me any more. Conversely, Baran’s work in the area of pyrrole-imidazole alkaloids is still facinating, even though I’ve blogged about it more than a few times! What we’re looking at here, though, isn’t …

Still In The RBF »

[14 Aug 2011 | 19 Comments | 17,140 views]
N-Methylwelwitindolinone C

Garg, Huters, Quasdorf, Styduhar. JACS, 2011, ASAP. DOI: 10.1021/ja206538k
Technically beaten to the finish-line by Rawal (JACS in March), but still the first asymmetric synthesis of the Welwitindolinone family, this synthesis is one of many contributing to a hell of a year for Neil Garg.  I think the key to the synthesis was picking the perfect starting point – and dealing with poor yields that get you seriously further forwards.
That critical starting point is  fantastically smelling (S)-Carvone.  Not only does this make the lab (and presumably the chemist, his notebook, …

Guest Post, Still In The RBF »

[6 Aug 2011 | 17 Comments | 15,659 views]
Omphadiol

Romo, Liu. ACIEE, 2011, 50, 7537-7540. DOI: 10.1002/anie.201102289
Guest Blogger: SPF
What if I’d ask you to synthesize this little molecule with six neighbouring stereocenters from biologically available material? Oh, by the way you can’t use any protecting groups and keep it short! Sounds impossible? Not according to Romo et al.. They’ve achieved the synthesis of this stereo-dense molecule in 10 steps from (R)-carvone (Mmmhhh spearmint). (+)-Omphadiol belongs to the africanane (guess where they grow) family of sesquiterpenes. Its brothers and sisters show some significant bioactivity, but due to insufficient …