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Articles tagged with: terpene

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[14 Jan 2012 | 33 Comments | 22,110 views]
Fusarisetin A

Li, Deng, Zhu, Lu, Yu. JACS, 2011, ASAP. DOI: 10.1038/nchem.1196  
Just take a quick look at that target and consider that the synthetic route I’m about to summarise took thirteen steps.  I’m fairly stunned – I read the top-line number in the abstract, and immediately thought that they must have started with an advanced intermediate or degredation product, but no – the synthetic action (like many natural product syntheses) begins with Citronellal.  Sure, only three of the rings are carbocyclic, but there’s a lot going on here, so lets get into …

Featured, Still In The RBF »

[7 Dec 2011 | 23 Comments | 21,433 views]
Taxane Skeleton

Baran, Mendoza, Ishihara. Nature Chem., 2011, EarlyView. DOI: 10.1038/nchem.1196   
Hmm… I’m still not convinced about whether I should really post on this paper, but I’m interested in it, so to hell with the rules!  What we’ve got here is a sort-of meta-synthesis; Baran doesn’t actually make any of the taxane natural products, but demonstrates an extremely neat synthesis of a potential common precursor.  The theory behind the work is related to previous Baran diatribes, where he points out that too many steps in syntheses simply oxidise and reduce the same …

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[14 Aug 2011 | 19 Comments | 16,904 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 | 15,390 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 …

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[2 Dec 2009 | 26 Comments | 14,762 views]
9-Isocyanopupukeanane

Corey, Brown. Org. Lett., 2009, ASAP. DOI: 10.1021/ol9025793.  . Corey, Behforouz, Ishiguro. JACS., 1979, 101, 1608–1609. DOI: 10.1021/ja00500a048. 
Again, it’s been a while since I blogged, and this time the excuses are two-fold.  First of all, I moved home recently to the leafy London suburb of Surbiton (saaf-wess, for natives…), and have been without my computer, interweb access and beer, all three of which are required for blogging.  However, more critically, there’s been a real dearth of total synthesis in the ASAPs, so much so that this paper isn’t even a formal synthesis (not in the title at …

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[17 May 2009 | 53 Comments | 20,081 views]
Eudesmane Terpenes

Baran, Chen. Nature, 2009, AOP. DOI: 10.1038/nature08043.
They say that the best defence is a good offence, so I’m going to start latterly – and remind (somewhat forcefully, if necessary) all prospective commenters that the folks at Nature decreed that this paper is worthy.  That’s good enough for me, so let’s avoid the tired arguments about suitability… </pre-emptive rant>
Anyway, what we’ve got here is typical of Baran – re-examination of chemical methodology of the past, and modernisation to solve problems in an orthogonal fashion.  Breaking that down, …