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Articles tagged with: Stille

Still In The RBF »

[20 Dec 2009 | 27 Comments | 14,436 views]
(iso)Bongkrekic Acid

Ley, Francais, Leyva, Etxebarria-Jardi. Org. Lett., 2009, ASAP. DOI: 10.1021/ol902676t.
For those UKian readers out there, there’s a fittingness to my posting a Cambridge paper following an Oxford last week.  Having spent a bit of time at both, it’s hard for me to pick a particular allegience, but I guess I have to go light blue, and congratulate the boys for their dug-in performance at Twickenham a few weeks back.  But I am particularly lucky to have been at both, as their approach to organic chemistry was so markedly different. …

Still In The RBF »

[31 Oct 2009 | 105 Comments | 51,368 views]
Vinigrol

Baran, Maimone, Shi, Ashida. JACS, 2009, ASAP. DOI: 10.1021/ja908194b.
Yep, it’s done.  Surprised?  You shouldn’t be, not after the Angewandte published last year, which was tantalisingly close to the natural product.  For the uninitiated, this target has been on grant-proposals world-wide for the last twenty years, subsequent to it’s isolation in 1987, culminating in nearly twenty ‘syntheses towards’ type papers, but no cigar until now.  And don’t think that those incomplete approaches were by the Bionic Bros – were talking big names like Paquette.  So what did Baran do to triumph? …

Still In The RBF »

[15 Sep 2009 | 23 Comments | 15,623 views]
Hirsutellone B

Nicolaou, Sarlah, Wu, Zhan. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200903382.
Yep, I took my sweet time about blogging this.  Hell, it’s been over a week since my last post… no excuses, I’ve been living on Spotify, and trying to justify buying a Canon 7D.  So not reading much chemistry then, but I did see this (actually, it was my former labmate, Phil, who linked-me-up).  A damn nice piece of work, with an interesting mix of old and new chemistry.  The target was found in a fungus, but was …

Still In The RBF »

[25 Aug 2009 | 8 Comments | 12,056 views]
Sorangicin A – pt. 2

Smith, Dong, Brenneman, Fox. JACS, 2009, ASAP. DOI: 10.1021/ja9052366.
Read the first post?  Good.  Let’s get on with the one remaining fragment, a further DHP.  Work on this fragment was conducted via a coupling of an enone with the ready-elaborated sidechain – reaction that might be a little sluggish, as the enol functionality is again working against the group.  However, forming a cuperate of the vinyl bromide solved this, allowing a highly selective and reasonably high yielding reaction (60%, 20:1 d.r.).  BTW, the two fragments weren’t particularly …

Still In The RBF »

[23 Aug 2009 | 5 Comments | 10,218 views]
Sorangicin A – pt. 1

Smith, Dong, Brenneman, Fox. JACS, 2009, ASAP. DOI: 10.1021/ja9052366.
I thought I’d re-start after holiday with a tasty target, and sorangicin A certainly fits the bill.  It’s not often that I have to draw such an exotic structural motif into a target (though in reality it’s not far removed from a DHP); always a welcome feature in a synthesis.  But sorangicin A is more than just a structural challenge – it’s quite an antibiotic, with broad-spectrum activity against both Gram-positive and Gram-negative strains.  With the funding proposal …

Still In The RBF »

[30 Mar 2009 | 11 Comments | 10,897 views]
Vincorine

Qin, Zhang, Huang, Shen.JACS, 2009, ASAP. DOI: 10.1021/ja901219v.
It’s really nice to move on to a full paper this week after last weeks (lack of) communication nightmare, as it gives Yong Qin plenty of space to discuss his strategy for the synthesis of vincorine, including the missteps.  The target has seen quite a bit of action, having been completed by Vollhardt, Overman and Levy in the past, but Qin’s got quite a background in this family too.  In-case you’re sitting there thinking ‘I’ve seen this somewhere before…’, I’ll take …

Methods, Still In The RBF »

[25 Feb 2009 | 14 Comments | 14,699 views]
BE-43472B

Nicolaou, Lim, Becker. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900058.
Huh; you wait months for a Nicolaou synthesis, and then two come at once!  This little beastie and sporolide B dropped in Angewandte on consecutive days, both represented by abstracts drawn in the now familiar crayon-o-vision styling of La Jolla’s most-prolific chemist and photoshop abuser. Seriously, check this stuff out – this is on his home page!  The last time I saw anything like this I’d been over-doing both the ether and the geocities…

Of course, all this wouldn’t be …

Methods, Still In The RBF »

[10 Feb 2009 | 25 Comments | 14,053 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.

Still In The RBF »

[3 Apr 2008 | 14 Comments | 9,712 views]

Qin, Shen and Zhang, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800566.
Second showing in as many months for this popular alkaloid, this route from Yong Qin at the “Department of Chemistry of Medicinal Natural Products and, Key Laboratory of Drug Targeting, West China School of Pharmacy” (can’t get the website to work…) shows a few similarities to the recently covered route by Larry Overman, along with some interesting alternatives. Eschewing Overman’s ambitious palladium cascade designs, they went a bit old-school, planning a carbene insertion into an indole. However, …

Still In The RBF »

[13 Mar 2008 | 30 Comments | 13,935 views]

Paterson, Anderson, Dalby, Lim, Genovino, Maltas, and Moessner.ACIEE, 2008, EarlyView. DOIs: 10.1002/anie.200705565, 10.1002/anie.200705566.
Now I’ve been waiting for this ‘un… those of you who have been reading for a while will remember that I used to study at Cambridge University, and shared weekly meetings with the Paterson group. It’s certainly an ambitious target, with 21 stereocenters – and when they started the work, the absolute stereochemistry was yet to be assigned! Plenty of other groups are working on a synthesis of this beast, including …