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Articles tagged with: cycloaddition

Still In The RBF »

[11 Jun 2011 | 7 Comments | 10,993 views]
Aspidophylline A

Garg, Zu, Boal. JACS, 2011, ASAP. DOI: 10.1021/ja203227q
So – when one ‘old-schools-up’ a synthesis, is that a homage, or just ho-hum?  I guess it comes down to two things – the reactions used, and the overall synthetic strategy.  Use them in the correct manner, and it comes across as the sweetest synthesis; or alternatively as a [ctrl-C] [ctrl-V] bore-fest;  Garg’s synthesis of Aspidophylline A is most definitely the former.
The target is a member of a large family of alkaloids isolated in 2007, bearing the somewhat unusual furoindoline …

Still In The RBF »

[15 Feb 2010 | 18 Comments | 14,632 views]

Boger, Campbell, Zuhl, Liu. JACS, 2010, ASAP. DOI: 10.1021/ja908819q.
A busy week in the Boger group; it’s been a while since I blogged papers back-to-back from one group!  This target has clearly developed from their work in vindoline and vinblastine, using similar synthetic techniques.  Their interest in this target in particular was to assign the absolute stereochemistry; only one synthesis has been completed so far, and they didn’t check all the boxes in the submission form…
Synthetically, the first thing of note (for me at least!) is their synthesis …

Still In The RBF »

[26 Sep 2009 | 53 Comments | 19,864 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 »

[15 Sep 2009 | 23 Comments | 16,032 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 »

[14 Jul 2009 | 20 Comments | 11,885 views]
Polyanthellin A

Johnson, Campbell, Qi. JACS, 2009, ASAP. DOI: 10.1021/ja904136q.
Sorry for the lack of blogging, folks – I’ve been feeling a bit under the weather, but I assure you, it’s not H1N1…  However, it seems like the res of the world is getting on with it, with several nice syntheses in JACS just now.  Lyconadin A is headed for Chemistry World, later this month, whilst plicatic acid is line behind polyanthellin A. Hopefully, sticking the latter into the Tot. Syn. search box (operated by trained hamsters) will …

Still In The RBF »

[30 Mar 2008 | 16 Comments | 8,422 views]

Tadano, Takao, Hayakawa, Yamada, Yamaguchi, Morita and Kawasaki, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800253.
Mentioned in the comments, this tidy little synthesis features one hell of a tightly functionalised ring system, with seven contiguous stereocentres and a trans- trisubstituted olefin in a ten-membered ring. The biological activity seems impressive too: cytotoxicity and immunosuppressive activity, but the potency isn’t mentioned in this paper. This is actually the first synthesis of pestalotiopsin A, even though it’s recieved plenty of attention from the Procter and Paquette groups. Retro time:

Circumventing …