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Articles Archive for June 2009

Still In The RBF »

[28 Jun 2009 | 63 Comments | 40,896 views]
Himandrine

Movassaghi, Tjandra, Qi. JACS, 2009, ASAP. DOI: 10.1021/ja903790y.
Okay, I missed my ‘I’ll blog it by Saturday‘ deadline by a day, but it’s taken quite some time to get my head round these structures.  And beer.  However, I think I’ve got there – so ladies and gents – on with one of the best syntheses this year.
First up scheme-wise is a rather nice Suzuki coupling.  Taking a standard boronic acid, mixing in a vinyl-gem-dibromide, they achieved a selective E,E- product in cracking yield.  However, this came at …

Still In The RBF »

[23 Jun 2009 | 46 Comments | 15,589 views]
Gloeosporone

Jamison, Trenkle. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200902079.
When a target’s been made as many times as gloeosporone, it’s a good idea to come along with something new.  And when the people you’re following have a bit of a rep, it makes it doubly necessary.  How does Seebach (twice), Fürstner, Schreiber, Ley and Holmes make you feel?  Good thing Tim Jamison’s got quite a thing for a macrocycle, and an impressive creativity with them – as demonstrated in his synthesis of acutiphycin, covered here back in 2006.  He’s …

Still In The RBF »

[18 Jun 2009 | 53 Comments | 15,638 views]
Haouamine A

Baran, Burns, Krylova, Hannoush. JACS, 2009, ASAP. DOI: 10.1021/ja903745s.
Oh, we’re going way back here… a whole three weeks before I started blogging!  This brings us all the way back to Baran’s first conquest of haouamine A (and his eleventh paper), racemic, and in this JACS. It was followed up by an Angewandte two years later, but I’ve apparently only covered Weinreb’s synthesis, also back in 2006.  Part of the reason for all this interest is that the molecule seems to exhibit an unusual isomerism.  Baran realised …

Still In The RBF »

[13 Jun 2009 | 56 Comments | 16,069 views]
Napyradiomycin A1

Snyder, Tang, Gupta. JACS, 2009, 131, 5744. DOI: 10.1021/ja9014716.
Okay, it’s taken me far too long to get around to this article – I actually wrote the Chemdraw back when this article was in ASAP… but other stuff got in the way, like a little Nature paper from Baran.  However, it’s a damned nice paper, so it’s impossible for me not to go back and look at it properly.  The target here is an halogenated natural product, isolated from Streptomyces bacteria – so it’s not too surprising …

Methods, Still In The RBF »

[8 Jun 2009 | 27 Comments | 13,517 views]
Physostigmine & Convolutamydine E

Barbas, Bui, Syed. JACS, 2009, ASAP. DOI: 10.1021/ja903520c.
Now, this is a bit of a fib already. I’m not entirely sure of Barbas’ reason for calling this paper a ‘formal total-synthesis of physostigimine’, as, whilst it is a formal synthesis, he actually stops at another natural product, esermethole.  Now, this is fine – and it’s still a formal synthesis of physostigimine, but it is moreso a total synthesis of esermethole.  Why he felt the need to call this a formal synthesis I don’t know.
It’s a shame …

Chemistry World, Still In The RBF »

[5 Jun 2009 | 3 Comments | 5,964 views]
Kendomycin

Latest piece for the RSC in the June issue of Chemistry World, making a rather popular molecule [1, 2].

Still In The RBF »

[2 Jun 2009 | 24 Comments | 11,187 views]
Ricciocarpin A

List, Michrowska. Nature Chem., 2009, AOP. DOI: 10.1038/nchem.215.
Another rather short blog post, but why wax-lyrical when the synthesis is short and sweet?  Ben List is still hammering-away at his niche in organocatalysis, this time reporting a rather nice domino reaction.  The target of the synthesis is a isolate of a liverwort, and possesses “potent molluscicidal activity” – not a biological effect I’d come across before.  It turns out that this natural product spells doom for Biomphalaria glabrata water snails…  and we’re still at a loss.  Water …