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Articles Archive for February 2008

Still In The RBF »

[26 Feb 2008 | 48 Comments | 14,983 views]

Smith, Basu and Bosanac. JACS, 129, 14872 – 14874. DOI: 10.1021/ja077569l.
I felt like suggesting I was bullied into posting an entry on this synthesis, but the truth is that 1) it’s an awesome piece of work, and 2) I did ask for suggestions… So feeling suitably deferential, let’s look at the biological activity. Nothing particularly special in terms of the effect (cytotoxicity against the human cell lines P388 and lymphoid leukemia), but the numbers are fairly small: IC50 0.09 and 0.037 μg/mL. However, if we’re fair – …

Still In The RBF »

[21 Feb 2008 | 39 Comments | 15,276 views]

I realise this is a break in your usual Tot. Syn. programming, but I’ve been pondering… I know, it’s not healthy, and I should really get back to blogging another synthesis, but this kinda thing interests me. Y’see, after blogging the Danishefsky synthesis last week, and the Corey synthesis on Monday, I was intrigued by the differences in graphical representation of structures. Both were published in the same journal (JACS), in the same month, so one might expect a consistency of style, but not in this case. I’ve …

Still In The RBF »

[19 Feb 2008 | 22 Comments | 8,473 views]

Corey and Larionov. JACS, 2008, ASAP. DOI: 10.1021/ja8003705.
This article was mentioned in the comments for the previous post, and contains some quite remarkable chemistry. Corey himself has had quite a fascination with this class of natural products, having already completed (amongst others) Antheliolide A back in 2006. However, this work takes a somewhat alternative route to the trans-cyclooctene moiety, starting with a bit of primordeal organocatalysis – the Hajos-Parrish-Eder-Sauer-Wiechert reaction (see the Org. Syn. too)! Not only is this a nominee for the longest named reaction, …

Still In The RBF »

[12 Feb 2008 | 16 Comments | 6,932 views]

Danishefsky and Yu, JACS, 2008, ASAP. DOI: 10.1021/ja7113757.
I found this short synthesis remarkable for taking a modern twist on some resolutely old-school chemistry. I haven’t come across this particular family of natural products before, and Danishefsky doesn’t tell us too much about their properties, other than mentioning “varying degrees of antibiotic and antitumor activity”. I guess this means that we’re in for the chemistry, which involves one hell of a challenging Diels-Alder. I’m not going into the methodology here (but there is some discussion of it in …

Still In The RBF »

[6 Feb 2008 | 29 Comments | 22,144 views]

Woodward and Doering, JACS, 1944, 66, 849. DOI: 10.1021/ja01233a516; JACS, 1945, 67, 860. DOI: 10.1021/ja01221a051.
Williams and Smith, ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200705421.
It’s fair to say (in some respects at least) that this isn’t the freshest total synthesis report ever, but it’s certainly one of the most interesting, as a chapter of synthetic chemistry that has caused serious controversy has now been closed. This whole affair revolves around Woodward’s formal total synthesis of quinine, first published way back in 1944. His work with …