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Articles tagged with: Lewis-acid

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[14 Jan 2012 | 33 Comments | 21,668 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 …

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[7 Dec 2011 | 23 Comments | 21,240 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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[17 Jun 2010 | 11 Comments | 12,130 views]
Fawcettimine

Jung, Chang, Org. Lett., 2010, ASAP DOI: 10.1021/ol1009762.
Although the number of actual steps in a formal synthesis is (or at least should be) smaller than in a full total-synthesis, I often feel that the actual work is harder.  Afterall, one is directly comparing ones work with that of another researcher, and in this case Michael Jung has got his work cut-out.  There aren’t many professors whose work is truly that daunting, but Clayton Heathcock is one of them. Jung’s work intercepts the Heathcock synthesis eight steps from then …

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[28 Mar 2010 | 14 Comments | 16,967 views]
Actinophyllic Acid

Overman, Martin, Rohde. JACS, 2010, ASAP. DOI: 10.1021/ja100178u.
I don’t think there is a single academic whose syntheses I look forward to more than Larry Overman.  I’m not sure exactly why that it, but I think the main reason is the overall standard of his work, as well as his tendency to write fascinating and informing full-papers.  He’s also one of those professors who ‘owns’ a particular type of natural product; ‘Overman molecules’ are of course, alkaloids.
This paper not only discusses a ‘first synthesis’ in a racemic form, but also a …

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[10 Jan 2010 | 17 Comments | 13,837 views]
Isatisine A

Kerr, Karadeolian. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906632.
It’s always going to be a tough situation for the article I blog following something like Palau’amine, but this short and sweet synthesis by Michael Kerr of the University of Western Ontario (in the other London – which I visited in ’95) is as good as can be.  The rationale for it’s investigation is also pertinant, as it turns out that Isatisine A is a moderately active HIV isolate (EC50 of 38 ?m).  A secondary interest in the isolation was …

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[15 Sep 2009 | 23 Comments | 15,603 views]
Hirsutellone B

Nicolaou, Sarlah, Wu, Zhan. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200903382.
Yep, I took my sweet time about blogging this.  Hell, it’s been over a week since my last post… no excuses, I’ve been living on Spotify, and trying to justify buying a Canon 7D.  So not reading much chemistry then, but I did see this (actually, it was my former labmate, Phil, who linked-me-up).  A damn nice piece of work, with an interesting mix of old and new chemistry.  The target was found in a fungus, but was …