Someday we’ll all be free

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I’ve been searching the literature today, and came across this interesting paper about platensimycin. This antibiotic was only initially reported last year, but there are already a bunch of total and partial syntheses of it. So why do we need yet another synthesis of it? Because we always need more ways to synthesize molecules. Duh. This one, however, it particularly fun because it reports the synthesis of a key intermediate for platensimycin without using protecting groups (in 8 steps; ~10% yield compared to 10-16 steps and ~5-11% yield) and in a much more scale-up friendly manner (several steps are quantitative and require no purification). It makes me wonder if this protecting group-free idea (recently also reported by Baran et al.) is catching on, or if Tiefenbacher and Mulzer just have their eye on the prize (in terms of thinking about the chemical engineering side of making the molecule). What do you guys think? And is it even possible to dissect those two motivations?

The other fun thing about this paper is that it’s one of those syntheses where I want to get out my molecular model kit to see how all these 3D transformations occur.

Finally, another interesting thing I discovered in looking deeper into this story is that the molecule was only initially reported (in the literature) on May 18th, 2006, and the first total synthesis of the molecule was submitted for publication September 21st of that same year. Clearly, someone either has magic hands or had advance knowledge of the structure. For those of you in the synthetic field, how critical is it to get inside information on new structures that are found? And what’s the source in general – a friend who does this research, a talk at a conference, your own culture of bacteria? And what’s the price of this knowledge, or is it, like this synthesis, free?

Catherine (associate editor, Nature Chemical Biology)