Home » Archive

Articles tagged with: radical cyclisation

Still In The RBF »

[17 Oct 2009 | 57 Comments | 22,279 views]
Platensimycin

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 »

[6 Sep 2009 | 31 Comments | 17,760 views]
Minfiensine

MacMillan, Jones, Simmons. JACS, 2009, ASAP. DOI: 10.1021/ja9052366.
Now this is a popular target; I’ve covered syntheses by both Qin and Overman (with a related synthesis of vincorine by Qin too), both of which contain some really nice chemistry, and aren’t exactly lengthy.  However, this approach by MacMillan is incredibly concise, containing only nine steps, and starting with a commercially available indole.  To get to the key cyclisation precursor, a process of carbonylating the C-2 position by lithiation and addition of DMF, followed by a Horner-Wadsworth-Emmons olefination …

Still In The RBF »

[10 May 2009 | 31 Comments | 12,555 views]
Amphidinolide X

Lee, Jung. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900865.
Another month, another amphidinolide – but we’re getting pretty close to the end of the alphabet now.  Actually, I’m (as ever) being rather over-the-top – we’ve not actually covered that many, but X & Y (as well as being an affront to my ears) were blogged in 2006, where the focus was on the THF synthesis.  This is the case again with Eun Lee’s synthesis, which almost disregards the polyketide-style sections.
The key to his synthesis of the THF is a …

Still In The RBF »

[4 May 2009 | 58 Comments | 18,837 views]
Acutumine

Castle, Li, Tartakoff. JACS, 2009, ASAP. DOI: 10.1021/ja9024403.
First-time out for this complex little target – not big, but with five contiguous stereocenters, including a neopentylic chlorine and two quat-carb centers.  Enough to get busy with, then.  Biology-wise, Castle doen’t exactly wax-lyrical – he mentions selective T-cell cytotoxicty, and “antiamnesic-effects” (sounds good for a Saturday night-out), but that can’t have taken up much space in the grant application.
Let’s move on to the chemistry – stepping in at a rather advanced step in this Org. Lett., published in …