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Articles Archive for November 2008

Still In The RBF »

[29 Nov 2008 | 39 Comments | 10,010 views]

Shibasaki, Yamatsugu, Yin, Kamijo, Kimura and Kanai. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200804777.
A fifth appearance for my favourite drug ‘interloper’ in to this natural-product space; alarm bells shouldn’t be ringing – just cause I work in pharma doesn’t mean I’ve turned my back on natural products! Tamiflu is of course based on a natural product, shikimic acid – the starting point for the original synthesis. But as natural sources go, it’s rather hard to get hold of, and thus damned pricey (£248 for 5g on SA …

Still In The RBF »

[24 Nov 2008 | 41 Comments | 11,077 views]

Shair, Lee, and Nieto-Oberhuber, JACS, 2008, ASAP. DOI: 10.1021/ja8071918.
A third showing for everybodies favourite androstane, this offering from Matt Shair adds to the quantity of inovative chemistry used in it’s contruction. As a quick reminder, first up was Phil Baran, back in May; then came Nicolaou and Chen in August – along with several ‘studies towards papers’. However, rather than my going through it all again, have a look at this excellent review by Stefan Bräse which was in ACIEE last month.
If you read it through, …

Still In The RBF »

[17 Nov 2008 | 17 Comments | 9,470 views]

Tanaka, Yoshimitsu and Ino. Org. Lett., 2008, ASAP. DOI: 10.1021/ol802225g.
Looking at this article, the second thought I had (after being generally impressed with the key steps) was that I’d perhaps blogged this molecule before. I was right – it was one of the first I wrote, back in April of 2006 – by Trost. My writing style may have progressed since then (and I’ve certainly become more, umm, expansive, but I still knew quality when I saw it. Trost’s work centred on his manipulation …

Still In The RBF »

[8 Nov 2008 | 30 Comments | 12,725 views]

Chen, Gao and Wang. JACS, 2008, ASAP. DOI: 10.1021/ja808110d.
Now that’s an interesting architecture! I’ve always had a soft-spot for homosteroids like this (and cortistatin), as their construction can often include that brilliant mid-20th century chemistry that folks like Corey and Woodward made their names with.  However, for this particular natural product, Chuo Chen of the UT Southwestern Medical Center has used a real mixed bag of impressive reactions.
The target, a C-nor-D-homosteroid to be precise, is actually isolated from that marine goo that seems so prolific.  And like …

Still In The RBF »

[2 Nov 2008 | 16 Comments | 15,578 views]

Fujii, Ohno, Inuki and Oishi, Org. Lett., 2008, ASAP. DOI: 10.1021/ol8022648.
Fancy making your own LSD?  You could do a lot worse that this prep from Kyoto University.  Of course, they don’t actually make the lysergic acid diethylamide, but I’m sure there’s a way to form that amide… Anyway, we should probably stick to the actual paper, and leave the class-A for another time.  I’m sure we’re all aware of the biological activity of some of the members of the ergot alkaloid family, but did you know about …