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Articles tagged with: hypervalent iodine

Still In The RBF »

[14 Aug 2011 | 19 Comments | 17,979 views]
N-Methylwelwitindolinone C

Garg, Huters, Quasdorf, Styduhar. JACS, 2011, ASAP. DOI: 10.1021/ja206538k
Technically beaten to the finish-line by Rawal (JACS in March), but still the first asymmetric synthesis of the Welwitindolinone family, this synthesis is one of many contributing to a hell of a year for Neil Garg.  I think the key to the synthesis was picking the perfect starting point – and dealing with poor yields that get you seriously further forwards.
That critical starting point is  fantastically smelling (S)-Carvone.  Not only does this make the lab (and presumably the chemist, his notebook, …

Still In The RBF »

[18 Apr 2010 | 24 Comments | 17,120 views]

Bradshaw, Bonjoch, Etxebarria-Jard?´. JACS, 2010, ASAP. DOI: 10.1021/ja101994q.
It’s been a while since I wrote about a synthesis from Spain, so it’s nice to return with a rather sweet synthesis from the labs of Josep Bonjoch and his compatriot, Ben Bradshaw. Their efforts have been focused towards a sub-set of diterpenoids produced by Aspergillus, in which the decalin ring junction contains a pair of quaternary carbons.  That’s a pretty significant challenge by itself, but the rest of the decalin in subsituted in an all cis- arrangement, making for …

Still In The RBF »

[28 Feb 2009 | 21 Comments | 17,657 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 …