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Articles tagged with: medium-ring

Still In The RBF »

[2 Jul 2011 | 23 Comments | 20,468 views]
Loline

Trauner, Cakmak, Mayer. Nat. Chem., 2011, 3, 543. DOI: 10.1038/nchem.1072
Simple tricyclic morpholine derivative with four stereocenters. Can’t take that much effort, can it? Well, yes it can – and it’s amazing how tricky this little beastie is! Trauner explains in the informative introduction that only one successful synthesis has been completed – taking twenty steps to get to the racemic target. Clearly that leaves the team in Germany with a lot of room for improvement.

The team made the first intermediate in the scheme …

Still In The RBF »

[14 Jul 2009 | 20 Comments | 11,783 views]
Polyanthellin A

Johnson, Campbell, Qi. JACS, 2009, ASAP. DOI: 10.1021/ja904136q.
Sorry for the lack of blogging, folks – I’ve been feeling a bit under the weather, but I assure you, it’s not H1N1…  However, it seems like the res of the world is getting on with it, with several nice syntheses in JACS just now.  Lyconadin A is headed for Chemistry World, later this month, whilst plicatic acid is line behind polyanthellin A. Hopefully, sticking the latter into the Tot. Syn. search box (operated by trained hamsters) will …

Still In The RBF »

[20 Apr 2008 | 29 Comments | 8,700 views]

Toste, Radosevich, Chan and Shih, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800554.
Another paper from the Toste group that doesn’t use recycled Rolex watches in any of the steps. Indeed, the metal of choice today is vandadium – read-up on the methodology in this tasty JACS from 2005. Anyway, the target is octalactin A, a medium ring lactone with a bit of murine melanoma and colon tumor busting activity. Previous syntheses by Buszek, Clardy, Shiina and my boss with Andy Holmes, so it’s certainly seen …