Comments on: Hyperforin http://totallysynthetic.com/blog/?p=2248 4,512 Ph. D. students died to make this blog... Thu, 09 Sep 2010 08:39:52 -0600 hourly 1 http://wordpress.org/?v=3.0 By: PowerfulDarkMagic http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-294088 PowerfulDarkMagic Sat, 10 Apr 2010 16:16:39 +0000 http://totallysynthetic.com/blog/?p=2248#comment-294088 Could someone please post the link for the SI? Thanks :) Could someone please post the link for the SI? Thanks :)

]]> By: RBG http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-291288 RBG Wed, 24 Mar 2010 14:12:27 +0000 http://totallysynthetic.com/blog/?p=2248#comment-291288 Can someone explain to me what "how-to-fuck-up-your-Swern-Oxidation type conditions" are? Apparently I'm the only person who has never been warned about them. On the synthesis, yes, it's more a tribute to perseverance than elegance, but it's the first enantioselective synthesis of ANY member of this class. Almost certainly, groups known for their synthetic prowess have tackled hyperforin over the years, but only Shibasaki's group has crossed the goal line. They definitely deserve their kudos for this one. Can someone explain to me what “how-to-fuck-up-your-Swern-Oxidation type conditions” are? Apparently I’m the only person who has never been warned about them.

On the synthesis, yes, it’s more a tribute to perseverance than elegance, but it’s the first enantioselective synthesis of ANY member of this class. Almost certainly, groups known for their synthetic prowess have tackled hyperforin over the years, but only Shibasaki’s group has crossed the goal line. They definitely deserve their kudos for this one.

]]> By: Madforit http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-280205 Madforit Fri, 22 Jan 2010 17:14:39 +0000 http://totallysynthetic.com/blog/?p=2248#comment-280205 Impressive... Impressive…

]]> By: stork naked http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279951 stork naked Wed, 20 Jan 2010 14:16:36 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279951 tough target, danishefsky/garsubellin was more striking tough target, danishefsky/garsubellin was more striking

]]> By: European Chemist http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279947 European Chemist Wed, 20 Jan 2010 11:42:37 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279947 This indeed gets very stepy. The overall approach is quite nice, but the way they solved the problems encountered makes it look like the students involved really suffered to get this through. Anyway, let's not underestimate the target's complexity and sensitivity. PS: Didn't read the SI, but does 66% over 3 cycles for the tandem MOM deprotection/hydromethoxylation of the double bond probably mean stopping conversion at close to 30% to avoid problems with the other prenyl double bond?... so much for "highly chemoselective" then... This indeed gets very stepy. The overall approach is quite nice, but the way they solved the problems encountered makes it look like the students involved really suffered to get this through. Anyway, let’s not underestimate the target’s complexity and sensitivity.

PS: Didn’t read the SI, but does 66% over 3 cycles for the tandem MOM deprotection/hydromethoxylation of the double bond probably mean stopping conversion at close to 30% to avoid problems with the other prenyl double bond?… so much for “highly chemoselective” then…

]]> By: Needles http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279935 Needles Wed, 20 Jan 2010 04:19:47 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279935 Great example of why methods people should focus on methods. Great example of why methods people should focus on methods.

]]> By: rings'N'things http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279930 rings'N'things Wed, 20 Jan 2010 02:48:18 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279930 Porco's work makes this look just plain silly Porco’s work makes this look just plain silly

]]> By: The Next Phil McGroin http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279900 The Next Phil McGroin Tue, 19 Jan 2010 22:29:37 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279900 Really impressive work. I have not read the paper yet, so maybe I am wrong, but based on this recap they did this work using primarily disconnections developed before this century. Kudos. Really impressive work. I have not read the paper yet, so maybe I am wrong, but based on this recap they did this work using primarily disconnections developed before this century.

Kudos.

]]> By: antiaromatic http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279892 antiaromatic Tue, 19 Jan 2010 19:18:36 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279892 This is typically the case as one of the protons on the cyclohexanone is essentially always aligned properly for deprotonation (i.e. axial), whereas in the acyclic systems, the free rotation makes this much more difficult and less likely. This is typically the case as one of the protons on the cyclohexanone is essentially always aligned properly for deprotonation (i.e. axial), whereas in the acyclic systems, the free rotation makes this much more difficult and less likely.

]]> By: European Chemist http://totallysynthetic.com/blog/?p=2248&cpage=1#comment-279883 European Chemist Tue, 19 Jan 2010 17:29:54 +0000 http://totallysynthetic.com/blog/?p=2248#comment-279883 Exactly - and enolisation of the aldehyde is unproductive since attack onto the neighbouring carbonyls would give 4-membered rings. Exactly – and enolisation of the aldehyde is unproductive since attack onto the neighbouring carbonyls would give 4-membered rings.

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