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Articles Archive for April 2009

Chemistry World, Still In The RBF »

[30 Apr 2009 | 16 Comments | 9,817 views]
(+)-11,11′-Dideoxyverticillin A

Latest piece for the RSC in the May issue of Chemistry World

Still In The RBF »

[21 Apr 2009 | 106 Comments | 44,616 views]
Agelastatin A Pt. 3

Du Bois, Wehn. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200806292.
Our third visit to this tightly functionalised little molecule (one – Trost, two – Tanaka, Yoshimitsu), that sterotetrad certainly brings in the players.  I’m not going to go into the biology (hit up the Tanaka post for that), so let get straight into the synthesis.  Du Bois kicks off with an opening of an optically active, bicyclic lactam (2-Azabicyclo[2.2.1]hept-5-en-3-one) – which is commercially available, but not exactly cheap.  Good thing the synthesis is so short…  Protection, reductive ring-opening and …

Still In The RBF »

[18 Apr 2009 | 102 Comments | 29,098 views]
Kapakahines B and F

Baran, Newhouse, Lewis. JACS, 2009, ASAP. DOI: 10.1021/ja901573x.

It’s always nice to be surprised by a synthesis dropping from nowhere… even though the commenting team here at Tot. Syn. mentioned an impeding Baran synthesis of an Indole-containing natural product.  And here it is, breaking a unmentioned Tot. Syn. rule – I don’t do peptides.  I’ve never mentioned this before, and no one has ever complained, so I guess I’m not the only one!  Kapakahine B gets out of this quandry by also featuring a rather tasty tetracyclic …

Editorial »

[16 Apr 2009 | 34 Comments | 11,877 views]
Tot Syn was on holiday – and is three!

Tot Syn is three!
Remarkable!  I’m astonished that the gig has lasted this long, and that you lovely reader keep reading my stream-of-conciousness.  Thanks!  And BTW, you (yes you!) are one of 33,000 people reading this month – which I reckon is a significant percentage of the chemically minded populous.  So what’s changed over those years?
1.  The theme.  Lots.  Sorry – I like to think I’m a bit of web-designer, but I promise I’ll limit the changes to once a year…
2.  The nationality of my readers:

United States  15,517
Japan  3,794
United Kingdom  3,194
Germany  …

Still In The RBF »

[5 Apr 2009 | 55 Comments | 34,890 views]

Corey, Shenvi. JACS, 2009, ASAP. DOI: 10.1021/ja901400q.
It was Corey that first brought this website properly off-topic back in 2006 with his synthesis of Tamiflu, which of course, isn’t a natural product (but is thusly derived).  It’s a similar situation with this target, 7-methylomuralide, which is a derivative of muralide, a target quite popular with Corey (with syntheses back in ’98 and ’03).  In this case, a simplification was made to ‘racemise’ the C-7 methyl group by converting it into a gem-dimethyl group – and retaining most of …

Chemistry World, Still In The RBF »

[2 Apr 2009 | 2 Comments | 6,844 views]
Chemistry World: Hopeahainol A and Hopeanol

Latest piece for the RSC in the April issue of Chemistry World