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Still In The RBF »

[23 May 2010 | 4 Comments | 9,213 views]
Complanadine A part II

Siegel, Yuan, Chang, Axelrod, JACS, 2010, 132, 5924 DOI: 10.1021/ja101956x.
It’s finally time to examine the second synthesis of Complanadine A, and I have to say that this route couldn’t be further removed from the Sarpong synthesis.  Of course Siegel’s route takes advantage of the dimeric nature of the target, but it’d be more worrying if he didn’t.
The synthetic action begins with a rather nice alkylation. Starting with a unsymmetrical cyclohexanone, alkylation could have occurred on either (or both) sides of the carbonyl.  By using a sulfide, the deprotonation is …

Still In The RBF »

[4 May 2010 | 43 Comments | 17,919 views]
Complanadine A part I

Sarpong, Fischer. JACS, 2010, 132, 5926 DOI: 10.1021/ja101893b.
It’s quite hard to explain the phenomenon of simultaneous publication to people outside of chemistry, ’cause it simply isn’t easy to rationalise.  This is now twice in as many months, as Englerin A took my fancy in this month’s Chemistry World.  I’ve never been in the situation of working on a target with rival groups bearing down on me, but it must be quite punishing (I took the slightly easier option of working on a target that 1. had …