B.R.S.M. The Battlefield Earth of organic chemistry blogs

19Jun/1213

A Birthday Surprise for K. C. Nicolaou

Update 1930, 20-06-12: Just noticed a mistake in my haplophytine structure (cdx, png and jpg) - a mesyl group where there should be an OH. If you've already downloaded/printed this please get the new, corrected version before continuing. Sorry!

Also, check out the first entry, from DrFreddy over at Synthetic Remarks!


Before you hurry to  check JACS, I made this myself. The image, that is.

The ongoing trend towards more colourful graphical abstracts is a perennial topic for discussion around the blogosphere.[1] Rather than draw attention to recent crimes against chemical decency, many of which can be found at TOCROFL, I am today proposing something new.[2] As many will know, the current spate of increasingly lurid abstracts can be traced to one man, American Cypriot and legendary synthetic chemist K. C. Nicolaou. But when did it all start? The cover of Classics in Total Synthesis I, published in 1996, appears to be free of such visual pollution, but it seems that by 2003 when Classics II and his autobiographical Tetrahedron prize essay were published that the inveterate colouring in had begun, and his papers are now rarely seen without it. However, I'm not going to join the online castigation of this questionable new form of art. Far from it. In fact, as it's KCN's birthday in a little over two weeks from today, I propose the WORLD'S FIRST CHEMICAL ABSTRACT COLOURING COMPETITION!

Filed under: Ask the audience, Fun | 13,327 views | 13 comments Continue reading
20Nov/1110

Taxol Time Again: What now, Phil?

Update 20-11-2011: Reference added and a couple of mistakes removed. Why can I never see those the first time?

Scalable Enantioselective Total Synthesis of Taxanes

Baran et al., Nature Chemistry, 2011, [PDF][SI][GROUP]

 

The taxanes are a large family of 350 or so natural products, of which the best known is taxol itself, a multibillion dollar anticancer drug with a rich and storied history, whose name and distinctive tetracyclic system are instantly recognisable to most organic chemists. Taxol itself has already been the subject of 7 epic total syntheses (see BRSM Reviews: Taxol In 10 Minutes if you need a quick reminder), all using conventional functional group lead approaches to bond formation. Nature's (and Phil's) approach is a bit different, though, as we'll see.

Filed under: Current Literature, Total Synthesis | 11,602 views | 10 comments Continue reading
20Nov/119

BRSM Reviews: Taxol In 10 Minutes

 

If you're reading this then I reckon you've probably heard of taxol, as it's one of the most talked about synthetic targets of all time. It's a molecule with a fascinating history, from its isolation and structural assignment in 1971, to discovery of its potent activity and interesting mode of action, and the ensuing scrabble to solve the supply problems plaguing its development as a drug.[1] Its rise to success as a billion dollar pharmaceutical was stellar, and is one of my favourite examples of how useful and important synthetic organic chemistry is. Although it's been 5 years since the most recently reported synthesis of taxol, last week's Baran synthesis of taxadiene (following his cyclase-oxidase mimic plan for elaboration of this hydrocarbon into taxol) seems to have again gotten chemists talking excitedly about this target. After overhearing things like 'didn't Nicolaou make it first?', 'there've only been x syntheses so far' (where x is 0-6) and other such misinformation in our office I've decided to take action. Yes, there are already numerous reviews, book chapters and even entire books on this subject, but it seems that a lot of people don't have the time or inclination to read them. So, here's a brief summary of the 7 syntheses published so far, in the order they were completed. Hopefully this'll help put recent developments in perspective.

Filed under: BRSM Reviews, Literature, Total Synthesis | 13,184 views | 9 comments Continue reading