A snapshot of the chemical blogosphere

I want to show the mathematicians the vibrancy and value of the chemical blogosphere so – at random – I picked today’s TotallySynthetic. By chance it’s very fitting as it is a review of a paper by one of the blogospheric heroes – Tenderbutton (== Dylan Stiles). Dylan wrote a fascinating and idiosyncratic blog for over a year until his supervisor and pressure of work combined to stop him – fittingly he has a regular blogging column for a chemical publisher. Here’s a flavour of the current post which I’ll show tomorrow:
== Excerpt (with some deletions) from TotallySynthetic Blog ==

Spirotryprostatin B

27 June 2007
Trost, and Stiles. Org. Lett., 2007, ASAP. DOI: 10.1021/ol070971k.
He’s done it . Those of us who read Tenderbutton from the start will have known of Dylan’s work on this tasty little number, and he’s done it proud. Eight steps to the natural product; we’ll start with step one (or rather, the first non-literature step):

We’ve looked at Otera’s catalyst before, but as a quick reminder, it’s a funky trans-esterification catalyst. It’s been known for a little while, and the mechanism is in this JOC article. Nice to see it being used; what was it like to handle, Stiles?
[… SNIP CHEmICAL DETAILS …]
Good job, old chap!

10 Responses to “Spirotryprostatin B”

1. milkshake Says:
   June 28th, 2007 at 1:56 A lovely detail is that a simple oxindole was used as a starting material…
2. the dude Says:
   June 28th, 2007 at 2:32 Could someone (maybe even Dylan) comment … Why can’t you use any of the plethora of other esterification catalysts? Thanks.
3. provocateur Says:
   June 28th, 2007 at 2:32 just a doubt…how is otera’s catalyst superior to the usual transesterification catalyst , titanium isopropoxide?
4. Spiro Says:
   June 28th, 2007 at 2:37 #1Absolutely. This guy, Trost, is plagiarizing Baran!
5. Spiro Says:
   June 28th, 2007 at 3:31 #2This is the one-million-dollar question!Provocateur’s comment about the “usual transesterification catalyst” makes me laugh. There are probably as many usual transesterification catalysts as there are Synth. Commun., Tet. Lett., Chem. Commun. or Org. Lett. articles titled “XYZ, a superactive catalyst for (trans)esterification of QWERTY-acids with YTREWQ-alcohols under mild conditions”.
   […]
   PPS: I have read Otero’s book on esterification : http://www.wiley.com/WileyCDA/WileyTitle/productCd-3527304908.html
   This is the poorest book I read from Wiley. After reading this book and many more articles on the topic I came to the conclusion that this field is a hoax.
6. kiwi Says:
   June 28th, 2007 at 10:11 #2, #3 – Oteras catalyst is a beaut, nice sparkling white crystals, stable as a rock. a shaved lab rat can make it on a scale of tens of grams…

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