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Articles tagged with: Heck

Still In The RBF »

[30 Oct 2011 | 38 Comments | 20,515 views]
Daphmanidin E

Carreira, Weiss. ACIEE, 2011, EarlyView. DOI: 10.1002/anie.201104681   
Now that’s a busy polycyclic ring-system!!  Three five-membered rings, two six-membered rings and one seven (depending, of course, on how one counts the ring sizes.  Anyone read the IUPAC Gold Book last night?) – adding up regardless of maths to one hell of a synthetic challenge.  And there’s even some token biological activity to aim for – this bad-boy has some moderate vasorelexant acitivity next to rat aorta.  (When the paper mentions ‘moderate’ activity, we can be pretty sure it does very little indeed…) …

Still In The RBF »

[11 Jun 2011 | 7 Comments | 10,879 views]
Aspidophylline A

Garg, Zu, Boal. JACS, 2011, ASAP. DOI: 10.1021/ja203227q
So – when one ‘old-schools-up’ a synthesis, is that a homage, or just ho-hum?  I guess it comes down to two things – the reactions used, and the overall synthetic strategy.  Use them in the correct manner, and it comes across as the sweetest synthesis; or alternatively as a [ctrl-C] [ctrl-V] bore-fest;  Garg’s synthesis of Aspidophylline A is most definitely the former.
The target is a member of a large family of alkaloids isolated in 2007, bearing the somewhat unusual furoindoline …

Still In The RBF »

[25 Feb 2010 | 30 Comments | 16,611 views]
Communesin F

Weinreb, Liu, Seo. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.200906818.
Quite a congested little beast, eh?  I felt that a 3D representation might help show the almost cage-like structure.  Also, having been at a Med-Chem conference for the last few days, I’ve been seeing everything in 3D.  I haven’t seen many molecules with this skeleton before, so I was surprised to see that it was isolated in Penicillium mold; however, this was found growing on a marine algae, so I guess that makes for some pretty special biosynthetic machinery. …

Still In The RBF »

[30 Mar 2009 | 11 Comments | 11,128 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 …

Still In The RBF »

[3 Apr 2008 | 14 Comments | 10,102 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 »

[5 Mar 2008 | 22 Comments | 11,612 views]

Overman, Dounay, Humphreys and Wrobleski. JACS, 2008, ASAP. DOI: 10.1021/ja800163v.
A far smaller target than the last we examined, but that’s still a very interesting architecture. Although the biological activity of this beast isn’t mentioned, similar natural products are found in traditional medicines, so perhaps it’ll do something interesting if you eat it. Their retrosynthesis is fairly ambitious, with a plan to use palladium couplings to complete two of the rings, and to do these reactions as part of a pair of tandem reactions.

The interesting chemistry …