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Articles tagged with: Sonogashira

Still In The RBF »

[6 Feb 2010 | 19 Comments | 12,320 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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[20 Dec 2009 | 27 Comments | 14,580 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. …

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[10 Nov 2009 | 19 Comments | 14,363 views]
Rubromycin

Brimble, Rathwell, Yang and Tsang ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200903316.
Now for something rather different… indeed, we’ve only got one stereocenter in rubromycin, and the synthesis is racemic.  However, one of the toughest and most commons lessons learnt when moving from total synthesis to medicinal chemistry is ‘just cause it’s flat, doesn’t mean the synthesis is easy’.  Frankly, rubromycin is a bitch to make, and has attracted many a chemist to their folly (seventeen papers referenced by Brimble here…).  However, tricky as it is, it’s not impossible – both Danishefsky …

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[22 Mar 2009 | 55 Comments | 18,226 views]
Ciguatoxin

Isobe, Hamajima. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200805996.
Also: 10.1055/s-2004-817769 , 10.1021/jo980088n , 10.1021/jo034021y, 10.1021/ol0600741 , 10.1016/j.tet.2007.03.012 , 10.1016/S0040-4020(03)00873-1, 10.1016/S0040-4020(02)00044-3… and many more.
As you can perhaps tell by the doi listings, this synthesis has been ongoing for quite some time.  And figuring out what was done, when, and how they did it has taken the best part of five hours now – the literature trail is like a tape worm, and as transparent as London tap water…  This seems to be a common theme for syntheses of marine …

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[28 Feb 2009 | 21 Comments | 17,257 views]
Sporolide B

Nicolaou, Tang, Wang. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900264.
The second of two papers published (almost) in succession in Angewandte from the KCN labs (also check out some more methodology in JACS – nice to see more methods from his group), sporolide B is the more challenging target, but devoid of any biological activity.  Nicolaou justifies his synthesis by discussing the biosynthetic origins of the sporolides, which are potentially products of enediyne cyclisation.  Convinced?  Perhaps…
Anyway, the structure is certainly interesting, being one of relatively few natural products that …