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Articles Archive for June 2011

Guest Post, Still In The RBF »

[16 Jun 2011 | 29 Comments | 19,370 views]
Cyanolide A Aglycon

Rychnovsky, Gesinski. JACS, 2011, ASAP. DOI: 10.1021/ja204228q
Guest Blogger: See-Arr-Oh
When I first saw the dimeric gamma-substituted pyran motif in this molecule, I said “Gotta be Rychnovsky” (or maybe Wender).   Throughout his career at UC-Irvine, Scott Rychnovsky has been the master of the TMS-promoted diastereoselective Prins cyclization, which he has applied to the synthesis of at least 10 macrolides.  Until now, however, none have been attempted sans protecting groups!
Cyanolide A was isolated in 2010, and it’s already been the target of four total syntheses.  Perhaps this is due to …

Still In The RBF »

[11 Jun 2011 | 7 Comments | 10,681 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 …

Chemistry World, Still In The RBF »

[5 Jun 2011 | 5 Comments | 10,207 views]
Conophylline

Fukuyama, Tokuyama, Han-ya. ACIEE, 2011, 50, 4884. DOI: 10.1002/anie.201100981
Not a full post, but it’s time to get some of these Chemistry World articles on here.  This once is the most recent, in the June issue, and follows Tohru Fukuyama’s synthesis on Conophylline – a really neat piece of work, especially when you consider how sensitive some of the functionality here is.  How many of you knew of the Polonovski-Potier reaction?