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Articles Archive for November 2009

Chemistry World, Still In The RBF »

[23 Nov 2009 | 13 Comments | 12,518 views]
Iriomoteolide 3a

A nice bit of metathesis and use of symmetry in this latest CW article, found in this month’s Chemistry World.  The original paper is here; also worth reading is a ‘core-synthesis’ by Chada Raji Reddy, which just dropped into Org. Lett.

Still In The RBF »

[17 Nov 2009 | 32 Comments | 15,192 views]
Fostriecin

McDonald, Robles. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902365n.
It’s been a little while, but there’s been nothing too exciting (total synthesis-wise) in JACS or ACIEE.  However, a quick glance in Org. Lett. produced a veritable cornucopia of syntheses, with this lesson in catalysis nudging to the fore.
The target is a newbie to this website and to me too – but not to the chemical community at large.  Indeed, the list of prior syntheses is quite unnerving for the prospective student-synthesizer, including Kobayashi, Boger, Cossy, Shibasaki, Reddy…  This brings a certain amount of knowledge, …

Still In The RBF »

[10 Nov 2009 | 19 Comments | 14,202 views]
Rubromycin

Brimble, Rathwell, Yang and Tsang ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200903316.
Now for something rather different… indeed, we’ve only got one stereocenter in rubromycin, and the synthesis is racemic.  However, one of the toughest and most commons lessons learnt when moving from total synthesis to medicinal chemistry is ‘just cause it’s flat, doesn’t mean the synthesis is easy’.  Frankly, rubromycin is a bitch to make, and has attracted many a chemist to their folly (seventeen papers referenced by Brimble here…).  However, tricky as it is, it’s not impossible – both Danishefsky …