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Articles Archive for February 2010

Still In The RBF »

[25 Feb 2010 | 30 Comments | 16,615 views]
Communesin F

Weinreb, Liu, Seo. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906818.
Quite a congested little beast, eh?  I felt that a 3D representation might help show the almost cage-like structure.  Also, having been at a Med-Chem conference for the last few days, I’ve been seeing everything in 3D.  I haven’t seen many molecules with this skeleton before, so I was surprised to see that it was isolated in Penicillium mold; however, this was found growing on a marine algae, so I guess that makes for some pretty special biosynthetic machinery. …

Still In The RBF »

[15 Feb 2010 | 18 Comments | 14,537 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 »

[6 Feb 2010 | 19 Comments | 12,407 views]
Phostriecin and/or Sultriecin

Boger, Burke, Haq. JACS, 2010, ASAP. DOI: 10.1021/ja9097252.
Figured it out already?  I bet it caused a few scratched-heads in Dale Boger’s group when, having made the published structure for Sultriecin, things didn’t tally-up.  We’ve discussed quite a few reassignments here over the years, but the majority are antipodal stereoclusters, or isomerisations at worst.  In this case, even the molecular formula was wrong!  The group may well have been suspicious before this point, though, as the related fostriecin, cytostatin and phospholine all contain the phosphate-mono ester that …