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Articles Archive for March 2009

Still In The RBF »

[30 Mar 2009 | 11 Comments | 11,131 views]
Vincorine

Qin, Zhang, Huang, Shen.JACS, 2009, ASAP. DOI: 10.1021/ja901219v.
It’s really nice to move on to a full paper this week after last weeks (lack of) communication nightmare, as it gives Yong Qin plenty of space to discuss his strategy for the synthesis of vincorine, including the missteps.  The target has seen quite a bit of action, having been completed by Vollhardt, Overman and Levy in the past, but Qin’s got quite a background in this family too.  In-case you’re sitting there thinking ‘I’ve seen this somewhere before…’, I’ll take …

Still In The RBF »

[22 Mar 2009 | 55 Comments | 18,386 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 …

Still In The RBF »

[16 Mar 2009 | 31 Comments | 14,283 views]
ent-Malbrancheamide B

Simpkins, Frebault and Fenwick. JACS, 2009, ASAP. DOI: 10.1021/ja900688y.
Sometimes, the sweetest syntheses come in the smallest packages, and with only one-and-a-bit pages, this is a very short paper.  However, Nigel Simpkins (now Haworth chair of Chemistry at Birmingham) manages to pack in quite a lot of cool stuff into that modest space.  A quick examination of the structure reveals a similarity to the stephacidin family, which has appeared in two previous posts here, one by Robert Williams, the other by Phil Baran.  However, there doesn’t appear to …

Still In The RBF »

[9 Mar 2009 | 14 Comments | 9,897 views]
Omaezakianol

Morimoto, Okita, Kambara. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200805857.
This isn’t the first poly-THF we’ve examined at Tot. Syn., but it is the most complex (see sylvaticin back in 2006 for the other example).  To the casual eye, the molecule looks deceptively symmetrical, but it isn’t.  In fact, only the two right-most THFs are alike, with the others differing in substitution, making the synthesis considerably more complex.  And to be frank, that’s the only reason we’re looking at it, as there doesn’t appear to be any biological activity.  …

Chemistry World, Featured, Still In The RBF »

[5 Mar 2009 | 12 Comments | 10,900 views]
Chemistry World: A Chlorosulfolipid

Latest piece for the RSC in the March issue of Chemistry World