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Articles Archive for September 2009

Still In The RBF »

[26 Sep 2009 | 53 Comments | 19,701 views]
Biyouyanagin A

Xie, Du, Li, Li. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200902908.
A second showing for this complex little target, Zhixiang Xie’s route uses the same end-game as that developed by Nicolaou two years ago.  However, getting to that point is a very different matter, using some quite powerful chemistry.  The RHS of the molecule is a distinct natural product – hyperolactone C, with the LHS also natural – zingiberene.  The latter was produced as in Nicolaou’s paper, but hyperolactone – the more challenging portion – was produced in a rather different …

Still In The RBF »

[20 Sep 2009 | 40 Comments | 16,699 views]
Lupeol

Corey, Surendra. JACS, 2009, ASAP. DOI: 10.1021/ja906335u.
Steroid chemistry, anyone?  They seem to back to the fore again – probably due to a bit of cortistatin – but looking to Corey is probably a good move, as he’s been working in this area for years.  And lupeol has been a pretty popular target too – look to Stork for his classic 1971 synthesis, with countless others working past lupeol en route to other steroids.  But more on that later –  we gotta make lupeol first.
A draw back …

Still In The RBF »

[15 Sep 2009 | 23 Comments | 15,903 views]
Hirsutellone B

Nicolaou, Sarlah, Wu, Zhan. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200903382.
Yep, I took my sweet time about blogging this.  Hell, it’s been over a week since my last post… no excuses, I’ve been living on Spotify, and trying to justify buying a Canon 7D.  So not reading much chemistry then, but I did see this (actually, it was my former labmate, Phil, who linked-me-up).  A damn nice piece of work, with an interesting mix of old and new chemistry.  The target was found in a fungus, but was …

Still In The RBF »

[6 Sep 2009 | 31 Comments | 17,893 views]
Minfiensine

MacMillan, Jones, Simmons. JACS, 2009, ASAP. DOI: 10.1021/ja9052366.
Now this is a popular target; I’ve covered syntheses by both Qin and Overman (with a related synthesis of vincorine by Qin too), both of which contain some really nice chemistry, and aren’t exactly lengthy.  However, this approach by MacMillan is incredibly concise, containing only nine steps, and starting with a commercially available indole.  To get to the key cyclisation precursor, a process of carbonylating the C-2 position by lithiation and addition of DMF, followed by a Horner-Wadsworth-Emmons olefination …