[6 Feb 2010 | 9 Comments | 1,630 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 …

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Still In The RBF »

[10 Jan 2010 | 14 Comments | 2,795 views]
Isatisine A

Kerr, Karadeolian. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906632.
It’s always going to be a tough situation for the article I blog following something like Palau’amine, but this short and sweet synthesis by Michael Kerr of the University of Western Ontario (in the other London – which I visited in ‘95) is as good as can be.  The rationale for it’s investigation is also pertinant, as it turns out that Isatisine A is a moderately active HIV isolate (EC50 of 38 ?m).  A secondary interest in the isolation was …

Still In The RBF »

[30 Dec 2009 | 108 Comments | 11,954 views]
Palau’amine

Baran, Seiple, Su, Young, Lewis and Yamaguchi. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200907112.
Y’know, I was kinda hoping for a bit of break between blog-posts this winter, as the amount of online publications tends to tail-off around the year-end.  However, not only have the publications been thick-’n’-fast (got quite a lot of material to get through), but up pops palau’amine.  I really did think that Angewandte would hold-off until sometime in early 2010, but here it is – and it lives up to Baran’s reputation.  I mean that in …

Still In The RBF »

[20 Dec 2009 | 27 Comments | 4,718 views]
(iso)Bongkrekic Acid

Ley, Francais, Leyva, Etxebarria-Jardi. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902676t.
For those UKian readers out there, there’s a fittingness to my posting a Cambridge paper following an Oxford last week.  Having spent a bit of time at both, it’s hard for me to pick a particular allegience, but I guess I have to go light blue, and congratulate the boys for their dug-in performance at Twickenham a few weeks back.  But I am particularly lucky to have been at both, as their approach to organic chemistry was so markedly different. …

Still In The RBF »

[15 Dec 2009 | 16 Comments | 3,803 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 …

Chemistry World, Still In The RBF »

[10 Dec 2009 | 4 Comments | 3,562 views]
Nakadomarin A

Yeah, I’ve not posted in a bit… Cephalostatin 1 is going into Chemistry World next month, but this months is also worth a read.  Darren Dixon’s synthesis of Nakadomarin A contains quite a few interesting transformation, and is very succinct.

Still In The RBF »

[2 Dec 2009 | 25 Comments | 5,626 views]
9-Isocyanopupukeanane

Corey, Brown. Org. Lett., 2009, ASAP. DOI: 10.1021/ol9025793.  . Corey, Behforouz, Ishiguro. JACS., 1979, 101, 1608–1609. DOI: 10.1021/ja00500a048. 
Again, it’s been a while since I blogged, and this time the excuses are two-fold.  First of all, I moved home recently to the leafy London suburb of Surbiton (saaf-wess, for natives…), and have been without my computer, interweb access and beer, all three of which are required for blogging.  However, more critically, there’s been a real dearth of total synthesis in the ASAPs, so much so that this paper isn’t even a formal synthesis (not in the title at …

Chemistry World, Still In The RBF »

[23 Nov 2009 | 12 Comments | 4,844 views]
Iriomoteolide 3a

A nice bit of metathesis and use of symmetry in this latest CW article, found in this month’s Chemistry World.  The original paper is here; also worth reading is a ‘core-synthesis’ by Chada Raji Reddy, which just dropped into Org. Lett.