Materials Girl: Whatever can go wrong, will…

Posted on behalf of Materials Girl:

Murphy’s Law, although highly applicable to the realm of chemistry, is demonstrated in all areas of life. Consider the [anticipated] tardiness of this post, attributed to my being away camping…

I had printed a stack of articles to study in relation to an upcoming post, much to the chagrin of my brother who protested his laser printer being in use for half an hour. However, being out in nature generally distracts one from reading about nature – “The Absorption of Water by Gelatin” would more accurately have been “The Absorption of Swamp by [my] Shoes”. That, however, is hardly an example of Murphy’s Law. The real irony was when people packed for the 110 degree Fahrenheit temperature at home, only to be met on the mountain with alternating heat and cold torrential rain. Fortunately, nature, Nature, and flash flood warnings are all exciting in their own way, so it wasn’t all that bad. Also, anything can remind me of chemistry, even something as trivial as pondering the dirt to water ratio in the various slurries of mud and grime covering the campsite. Once back in lab, I am likely to again start seeing things in terms of polarity, precipitates, and solvents…

The rain has begun in earnest again, and my pen is smudging over the notebook I am scribbling in. I shall type this up after getting home… Tell me your chemical stories involving Murphy’s Law, and perhaps how to avoid such occurrences – comments are wonderful.

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News from Nature Protocols

One of our featured protocols this month is for the partial reduction of electron-deficient pyrroles under both Birch (Li/NH3) and ammonia-free (Li/DBB) conditions using the formation of pyrrolines 2, 3 and 5 as examples (for reaction scheme click here). Pyrroles 2 and 5 have recently been published by Donohoe et al. as key intermediates in the of the biologically active natural products 1-epiaustraline, hyacinthacine A119and omuralide (also known as lactacystin lactone).

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Besides being an excellent protocol with beautiful photographs of reactions in progress, it is the first of our Nature Protocols to have associated with it two Network Protocols. These are for the preparation of the starting materials 1 and 4, namely the N-Boc pyrrole 2,5-methyl diester and the N-Boc pyrrole 2-ethyl ester.

Our Protocols Network has two components: protocols, such as these, that are uploaded by users (or suppliers); and comments that can be made both on the open access and the peer-reviewed content. If you would also like to participate, by uploading your favourite method or suggesting modifications to those that have already been published, you could follow the links from our homepage. A Guide to Authors for the Protocols Network also contains more information about this part of our content.

Bronwen (Nature Protocols)

References:

1. Donohoe, T.J. et al. Utility of the ammonia-free Birch reduction of electron-deficient pyrroles: total synthesis of the 20S proteasome inhibitor, clasto-lactacystin -lactone. Chem. Eur. J. 11, 4227–4238 (2005).

2. Donohoe, T.J. & Sintim, H.O. A concise total synthesis of ( )-1-epiaustraline. Org. Lett. 6, 2003–2006 (2004).

3. Donohoe, T.J., Sintim, H.O. & Hollinshead, J. A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline. J. Org. Chem. 70, 7297–7304 (2005).

4. Donohoe, T.J., Sintim, H.O., Sisangia, L. & Harling, J.D. An efficient synthesis of lactacystin -lactone. Angew. Chem. Int. Ed. 43, 2293–2296 (2004).

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