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Articles tagged with: aziridine

Still In The RBF »

[15 Dec 2009 | 16 Comments | 12,979 views]
1-Deoxynojirimycin and 1-Deoxyaltronojirimycin

Davies, Bagal, Lee, Roberts, Russell, Scott, Thomson. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902533b.
More of a post-ette than a full post, this tasty little nugget was found buried amongst effective reposts and updates.  Out there to give you a freaky sense of de ja vous are full papers on kendomycin, spirastrellolide, nakiterpiosin… finding something new was an effort!
What we’ve got here are a pair of closely related synthese of some poly hydroxylated piperidenes; notable for their glycosidase inhibitory effects.  Huh, I hear you say (actually, probably not – there are …

Still In The RBF »

[18 Jun 2009 | 53 Comments | 15,516 views]
Haouamine A

Baran, Burns, Krylova, Hannoush. JACS, 2009, ASAP. DOI: 10.1021/ja903745s.
Oh, we’re going way back here… a whole three weeks before I started blogging!  This brings us all the way back to Baran’s first conquest of haouamine A (and his eleventh paper), racemic, and in this JACS. It was followed up by an Angewandte two years later, but I’ve apparently only covered Weinreb’s synthesis, also back in 2006.  Part of the reason for all this interest is that the molecule seems to exhibit an unusual isomerism.  Baran realised …

Still In The RBF »

[21 Apr 2009 | 106 Comments | 43,509 views]
Agelastatin A Pt. 3

Du Bois, Wehn. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200806292.
Our third visit to this tightly functionalised little molecule (one – Trost, two – Tanaka, Yoshimitsu), that sterotetrad certainly brings in the players.  I’m not going to go into the biology (hit up the Tanaka post for that), so let get straight into the synthesis.  Du Bois kicks off with an opening of an optically active, bicyclic lactam (2-Azabicyclo[2.2.1]hept-5-en-3-one) – which is commercially available, but not exactly cheap.  Good thing the synthesis is so short…  Protection, reductive ring-opening and …