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Articles Archive for September 2007

Still In The RBF »

[30 Sep 2007 | 25 Comments | 16,338 views]

Snyder, Zografos and Lin. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200703333.  
This must be the simplest looking natural product I’ve drawn (since phenol, at least). However, it isn’t actually the goal of this work – rather, the goal is an array of targets based on resveratrol. If you are thinking that you might have read about resveratrol before – congratulate yourselves on reading the labels on red wine bottles thoroughly. Yep, it’s in red wine, and is known to combat inflammation, heart disease, aging, and cancer. Impressive. …

Still In The RBF »

[27 Sep 2007 | 33 Comments | 7,722 views]

Mulzer and Tiefenbacher. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702852.
It’s back! I’ve not blogged any total syntheses of platensimycin for ohh… at least three months, but this is some smart work by Johann Mulzer at the University of Vienna. Rather than complete a full synthesis, they’ve done the same as a few other groups and taken an intermediate from Nicolaou’s work and completed a synthesis of that structure. This is the same intermediate present in Snider’s synthesis, so I guess the consensus is that this is a good disconnection. High praise indeed!

The …

Still In The RBF »

[23 Sep 2007 | 26 Comments | 4,614 views]

A bit of house-keeping is being/about to be/might be done on Tot. Syn., so I thought I’d ask you lovely readers out there for a your opinions.
1. First off, and already implemented is InChi-ification of the structures on Tot. Syn. A nice introduction to InChi can be found here, but the jist of it is that they (InChi and the shorter InChiKey) are text identifiers for structures. You can use the InChi keys at the bottom of the post to quickly grab a copy of the structures.
I’ve done this not …

Still In The RBF »

[22 Sep 2007 | 15 Comments | 25,265 views]

Magnus, Cheung, Goldberg, Russell, Turnbull and Lynch. JACS, 2007, ASAP. DOI: 10.1021/ja0744448.
Another “big target”, another JACS… And this is another molecule that has been in the making for several years. Phil Magnus isn’t the first in this case – Nicolaou and Harran have both been there and done that. However, a worthy point made by Magnus is that both of the previous syntheses have involved rather inefficient H ring formation. That …

Still In The RBF »

[18 Sep 2007 | 24 Comments | 9,356 views]

Overman, Becker, Chua, Downham, Douglas, Garg, Hiebert, Jaroch, Matsuoka, Middleton and Ng. JACS, 2007, ASAP. DOI: 10.1021/ja074300t.
This is one mammoth piece of work. And that was the understatement of the week (which for me is saying something…). Loads of research groups have been working on this beast, including Weinreb, Heathcock, Cha, and Marazano. And to the uninitiated, it might look like a relatively simple target… However, this nice, fat 16 page JACS article shows how difficult it can be. Anyway, retro time:

As you can see, this retro is …

Still In The RBF »

[8 Sep 2007 | 47 Comments | 11,345 views]

Nicolaou, Lister, Denton and Gelin. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702695.
Recently isolated in an attempt to find the bioactive ingredients in some folk-medicines, the artochamins haven’t actually got that much biological activity. They’re described as being weakly cytotoxic, so let’s focus on the interesting ring system as our reason for synthesis. However, before leaping head-long into the chemistry, an interesting note is that the natural product is isolated as a racemic mixture, which suggests a non-enzymatic biosynthesis. Hmm…

The key substrate for this reaction is actually a symmetrical molecule, created very quickly …

Still In The RBF »

[2 Sep 2007 | 41 Comments | 10,726 views]

Toste, Linghu and Kennedy-Smith. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702695.
Not much room for maneuver in this tightly packed little alkaloid, and that makes the synthetic challange all the more attractive. Two previous syntheses: Inubushi and Heathcock, though both are racemic. Toste’s approach somewhat unsurprisingly uses gold catalysis in the key transformation, but there’s lots of other cool chemistry here. As ever with this type of chemistry, the first goal was a successful synthesis of the key substrate:

This is the first reaction that interested me. Toste references this silyl triflate promoted allene …