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Articles tagged with: rearrangement

Still In The RBF »

[18 Jan 2010 | 16 Comments | 16,853 views]

Shibasaki, Kanai, Shimizu, Shi, Usuda. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906678. ; Shibasaki, Kanai, Kuramochi, Usuda. Org. Lett., 2004, 6, 4387. DOI: 10.1021/ol048018s. 
Three amazingly tough targets completed in (almost) as many months – you can’t tell me that total synthesis is stifled.  Hyperforin has been staining the white-boards of many a lab for decades – the isolation (reported in Antibiotik…) was way back in ’71, and has resisted synthesis until now.  Shibasaki himself has been working on it for quite a while, as you’ll have seen in the header – a key …

Still In The RBF »

[17 Oct 2009 | 57 Comments | 22,632 views]

Njarðarson , McGrath, Bartlett, Sittihan. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200903347.
It’s back!  Twice in as many weeks, too, as KC has decided to drop the details on his many syntheses of platensimycin and platensin into a full JACS paper.  However, I’ve spent enough time looking at his work in this area, so it’s a pleasure to examine this synthesis by Jon Njarðarson of Cornell.  I should point out that I don’t feel that this is necessarily the best route, but it’s got some damn smart chemistry in it, so what …

Still In The RBF »

[20 Sep 2009 | 40 Comments | 16,987 views]

Corey, Surendra. JACS, 2009, ASAP. DOI: 10.1021/ja906335u.
Steroid chemistry, anyone?  They seem to back to the fore again – probably due to a bit of cortistatin – but looking to Corey is probably a good move, as he’s been working in this area for years.  And lupeol has been a pretty popular target too – look to Stork for his classic 1971 synthesis, with countless others working past lupeol en route to other steroids.  But more on that later –  we gotta make lupeol first.
A draw back …

Still In The RBF »

[18 Jun 2009 | 53 Comments | 16,034 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 …