tag:blogger.com,1999:blog-51846086760422068.post7440777541400276232..comments2024-03-28T08:37:08.964-07:00Comments on Open Flask: 11-Step Total Synthesis of Teleocidins B-1–B-4BaranLabhttp://www.blogger.com/profile/01806245988209508968noreply@blogger.comBlogger8125tag:blogger.com,1999:blog-51846086760422068.post-75260645803138093772019-01-15T12:53:37.827-08:002019-01-15T12:53:37.827-08:00Thanks for your question!
In general, the surface ...Thanks for your question!<br />In general, the surface area of the electrode in contact with the solvent is very important when setting up an electrochemical reaction. In the case of large glassware, we were not able to use the appropriate size of electrode. In addition, the efficiency of the agitation from the magnetic stir bar is also very important and we observed poor stirring in the upper part of the reaction mixture with the large glassware setup. This caused formation of Ni black on the upper side of electrode which we believe ultimately killed the reaction.<br /><br />Hugh NakamuraHugh Nakamurahttps://www.blogger.com/profile/07714922976244749736noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-80809168024563678882019-01-15T11:23:34.139-08:002019-01-15T11:23:34.139-08:00curious, what's your current theory for the di...curious, what's your current theory for the disastrous failure when trying scale up the e-amination in a bottle? Longbinhttps://www.blogger.com/profile/06079446548452418368noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-50049815372404237092019-01-14T10:08:01.909-08:002019-01-14T10:08:01.909-08:00Great question!
Answer #1: Basically, electron def...Great question!<br />Answer #1: Basically, electron deficient Ar-Br gives desired product in good yield because oxidative addition of Ni into electron deficient Ar-Br is easy. Therefore, we decided to use Ac group which is easy to remove after amination.<br />Answer #2: Good question! We thought about that. However, we thought there was a issue with the construction of the 9-membered ring due to strain. Thanks!<br /><br />Hugh NakamuraHugh Nakamurahttps://www.blogger.com/profile/07714922976244749736noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-44805117392317333292019-01-14T08:06:28.521-08:002019-01-14T08:06:28.521-08:00Very concise and elegant synthesis. Question #1: C...Very concise and elegant synthesis. Question #1: Can you use the use TIPS protecting group instead of acetate on the indole for the electrochemical transformation? Question #2: Can you make the flip the order of the steps; first make the amide bond with the aziridine and then do the macrocyclization at C3 of indole? Anonymousnoreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-49228601944491021732019-01-14T07:34:54.665-08:002019-01-14T07:34:54.665-08:00Thanks for your comment!
Hugh NakamuraThanks for your comment!<br /><br />Hugh NakamuraHugh Nakamurahttps://www.blogger.com/profile/07714922976244749736noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-59038675378227872262019-01-14T07:19:33.699-08:002019-01-14T07:19:33.699-08:00Thank you for your question!
Basically, secondary ...Thank you for your question!<br />Basically, secondary amine can be used for this electrochemical amination. However, in this particular case, simple L-valine Me-ester gave good yield!<br />Thanks for writing!<br /><br />Hugh NakamuraHugh Nakamurahttps://www.blogger.com/profile/07714922976244749736noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-28867204959303721112019-01-13T21:57:58.255-08:002019-01-13T21:57:58.255-08:00A really detailed and nice behind the scene look i...A really detailed and nice behind the scene look into the total synthesis. Congratulations to Teleocidin team! Supp info was excellent! loved it. Hope to see much more in near future.Anonymoushttps://www.blogger.com/profile/02161813597953776281noreply@blogger.comtag:blogger.com,1999:blog-51846086760422068.post-62820668313851393802019-01-13T20:19:07.942-08:002019-01-13T20:19:07.942-08:00Nice work! Does the amination work if you use N-Me...Nice work! Does the amination work if you use N-Me L-Valine? Or any secondary amine?TJnoreply@blogger.com