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Articles Archive for October 2009

Still In The RBF »

[31 Oct 2009 | 105 Comments | 51,836 views]
Vinigrol

Baran, Maimone, Shi, Ashida. JACS, 2009, ASAP. DOI: 10.1021/ja908194b.
Yep, it’s done.  Surprised?  You shouldn’t be, not after the Angewandte published last year, which was tantalisingly close to the natural product.  For the uninitiated, this target has been on grant-proposals world-wide for the last twenty years, subsequent to it’s isolation in 1987, culminating in nearly twenty ‘syntheses towards’ type papers, but no cigar until now.  And don’t think that those incomplete approaches were by the Bionic Bros – were talking big names like Paquette.  So what did Baran do to triumph? …

Still In The RBF »

[22 Oct 2009 | 30 Comments | 19,492 views]
Codeine

Magnus, Sane, Fauber, Lynch. JACS, 2009, ASAP. DOI: 10.1021/ja9085534.
I don’t think we’ve covered many targets I’ve actually ingested; and I’ve done most of the family too.  The morphine was a bit ‘meh’, as I was so out-of-it I couldn’t really appreciate it.  But the dihydrocodine was the good-stuff – really took the edge off my pluracy.  However, the withdrawal symptoms were kinda harsh.  Other members of this historic family of natural products include galanthamine and narwedine, neither of which I’ve encountered before.  Philip Magnus has, though, as …

Still In The RBF »

[17 Oct 2009 | 57 Comments | 22,297 views]
Platensimycin

Njarðarson , McGrath, Bartlett, Sittihan. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200903347.
It’s back!  Twice in as many weeks, too, as KC has decided to drop the details on his many syntheses of platensimycin and platensin into a full JACS paper.  However, I’ve spent enough time looking at his work in this area, so it’s a pleasure to examine this synthesis by Jon Njarðarson of Cornell.  I should point out that I don’t feel that this is necessarily the best route, but it’s got some damn smart chemistry in it, so what …

Still In The RBF »

[11 Oct 2009 | 36 Comments | 15,869 views]
Aigialomycin D

Barrett, Calo, Richardson. Org. Lett., 2009, ASAP. DOI: 10.1021/ol901979x.
Macrolactones?  From Barrett?  It’s not his usual fayre, but as is more normal, there is a twist in the synthesis.  I think most chemists (or at least me…), when presented with a target like aigialomycin, would think about buying-in the aromatic portion, and then trying to bolt on the styrene-type olefin and building around.  However, with his interests in reactive intermediates, Tony Barrett (of IC, London… just down the road), it comes of no real surprise to me that he …

Chemistry World »

[6 Oct 2009 | 14 Comments | 10,806 views]
Haplophytine

Okay, I’ve cheated you from a real post – but the Haplophytine story is a good one!  I had over 800 items in my Google Reader feed this morning, and I’m sure at least one of them will end out here!  In the mean time, check this piece out in Chemistry World.