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Articles tagged with: spiroketal

Still In The RBF »

[10 Nov 2009 | 19 Comments | 14,001 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 …

Still In The RBF »

[22 Mar 2009 | 55 Comments | 17,733 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 …

Methods, Still In The RBF »

[10 Feb 2009 | 25 Comments | 13,881 views]
Spirangien A

Paterson, Findlay and Noti. Chem. Asian J., 2009, ASAP. DOI: 10.1002/asia.200800445. Article PDF Supporting Information Group Website

It’s been a rather slow week in the world of total synthesis – I normally have a check on the ASAPs and EarlyViews in JACS and Angewandte every day in Google Reader (BTW, tune directly into my brainwaves under the ‘What I’m Reading’ section on the right…), and a bit less often, I’ll read Org. Lett., Chem. Comm. and OBC. If nothing turns up, then it’s on to Chem. Eur. J, JOC, and maybe even Tetrahedron… but today I took a far eastern excursion and found this distinctly Scottish paper (66% at least…). The thoughts going through my mind at this point were firstly, 1. I recognise that structure, 2. Ah, it’s Ian… 3. …and Alison – a former housemate from when I was living in Cambridge. It wasn’t just a house we shared, though – we also shared group meetings, and I remember this strucuture coming up, as Alison had just finished Dolastatin (that’s some old-school TotSyn right there…). I actually found the pentaene moiety the more interesting chunk, but of couse Ian Paterson’s all about the aldol.