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Articles tagged with: samarium diiodide

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[4 Sep 2011 | 64 Comments | 23,608 views]
Maoecrystal Z

Reisman, Cha, Yeoman. J. Am. Chem. Soc, 2011, ASAP. DOI: 10.1021/ja2073356 
A busy couple of weeks in the Reisman lab, it appears – really nice syntheses of the Cepharatines and 8-Demethoxyrunanine in Angewandte (doi: 10.1002/anie.201104487), but I decided to blog this tasty synthesis of Maoecrystal Z.  Of course, this isn’t the first member of that family that I’e blogged – the seminal synthesis of Maoecrystal V made my December 2010 column in Chemistry World.  I remember when I wrote that piece that the pseudo-3D structure used to represent the target annoyed …

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[25 Jul 2010 | 13 Comments | 15,300 views]
Galbulimima Alkaloids (-)-GB 13 and (+)-GB 16

Ma, Zi, Yu. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.201002299.
Why make one natural product when you can make two just as easily?  Or three in this case, but the headline syntheses are the Galbulimima Alkaloids GB-13 and GB-16 – notable members of a family that is getting some serious attention in pharma – one analogue is currently in phase III trials.  With all that potential, it’s not surprising that these beasties have seen quite a bit of synthetic attention; indeed, GB-13 was one of the first syntheses I …

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[3 Mar 2010 | 67 Comments | 23,468 views]
Echinopine A

Nicolaou, Chen, Ding, Richard. JACS, 2010, ASAP. DOI: 10.1021/ja9093988.
As I twittered the earlier today, redrawing KC’s crayonisation of Echinopine A took quite a while – but I think one needs to see both representations to get a feeling for the complexity here.  The unique [3.5.5.7] carbon skeleton is pretty special – apparently enough that no biological rationale is given for this work.  Perhaps I spend too much time looking a biological assay results these days…
So with nothing else for me to witter-on about, I’ll get into …

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[10 May 2009 | 31 Comments | 12,605 views]
Amphidinolide X

Lee, Jung. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900865.
Another month, another amphidinolide – but we’re getting pretty close to the end of the alphabet now.  Actually, I’m (as ever) being rather over-the-top – we’ve not actually covered that many, but X & Y (as well as being an affront to my ears) were blogged in 2006, where the focus was on the THF synthesis.  This is the case again with Eun Lee’s synthesis, which almost disregards the polyketide-style sections.
The key to his synthesis of the THF is a …

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[16 Apr 2008 | 43 Comments | 12,785 views]

Roulland, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800585.
Yep, just one name. And an impressive synthesis for just one chap (and I don’t think he even had the backing of “Bioic Bros. GMBH” like La Clair). Even the target has more names – this one was independantly isolated three times, gaining haterumalide NA and FR177391as alternative monikers (albeit with different optical rotations…). No mention is made of its biological profile in this paper, but a synthesis of the methyl ester by Snider in 2003 states “Haterumalide …