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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kriggy on January 25, 2019, 12:17:59 PM

Title: reaction to know for total synthesis
Post by: kriggy on January 25, 2019, 12:17:59 PM: Hey there,

im gonna go for 3month internship in total synthesis group which is kind of chemistry that I have no experience with. None at my place does total synthesis and I dont really want to embarass myself, my boss (he did postdoc in this group) and my department by not knowing during group meetings :D What are some more usefull reactions that are commonly used in total synthesis? Im thinking diels alder, aldol, but thats all I can think of.

thx
Title: Re: reaction to know for total synthesis
Post by: OrganicDan96 on January 25, 2019, 04:21:21 PM: this is a massive topic that i couldn't possibly tackle myself so i will point you to this website which will help
https://www.organic-chemistry.org/reactions.htm
Title: Re: reaction to know for total synthesis
Post by: wildfyr on January 25, 2019, 04:48:47 PM: Oof kriggy, this a monstrously complicated topic! You could read 3 textbooks and still not be ready! I would still start by trying to get through one of the classic retrosynthesis bibles.
Title: Re: reaction to know for total synthesis
Post by: hypervalent_iodine on January 25, 2019, 07:56:11 PM: I second reading through Classics in Total Synthesis. How useful it will be to you I don’t know. It is such a broad topic, I don’t think there is an adequate or easy way to prepare unless you know about what sort of compound you’re working with.
Title: Re: reaction to know for total synthesis
Post by: phth on January 26, 2019, 12:28:30 AM: Quote from: hypervalent_iodine on January 25, 2019, 07:56:11 PM
I second reading through Classics in Total Synthesis. How useful it will be to you I don’t know. It is such a broad topic, I don’t think there is an adequate or easy way to prepare unless you know about what sort of compound you’re working with.

Yeah, those are good books for directed studying.

One of the reactions that has stuck out in my mind:

https://en.wikipedia.org/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction

...Chain elongation by one carbon can be a pain.
Title: Re: reaction to know for total synthesis
Post by: kriggy on February 04, 2019, 04:27:40 AM: Thanks guys,
I know there is 1000s of reactions but I was wondering what are some "star reactions".. But I think its too broad topic to answer easily.
Title: Re: reaction to know for total synthesis
Post by: Babcock_Hall on February 04, 2019, 03:34:50 PM: Off the top of my head: Heck, Wittig, Wadsworth Horner Emmons, and Gilman Reagent coupling. As a sometime organophosphorus chemist, the Michaelis-Arbuzov, and the Michaelis-Becker reactions have been go-to reactions in the past.
Title: Re: reaction to know for total synthesis
Post by: wildfyr on February 04, 2019, 03:40:50 PM: Isn't cuperate chemistry like the Gilman a little outdated?

Let's not forget diels alder! There's plenty more than what you learn in sophomore organic. And I'll throw Michael addition in there too.
Title: Re: reaction to know for total synthesis
Post by: hypervalent_iodine on February 06, 2019, 01:18:44 AM: Quote from: wildfyr on February 04, 2019, 03:40:50 PM
Isn't cuperate chemistry like the Gilman a little outdated?

Let's not forget diels alder! There's plenty more than what you learn in sophomore organic. And I'll throw Michael addition in there too.

Pericyclic additions outside of DA are pretty big also. I had a quick look through some of the posters in our hallway (my group used to be 95% total synthesis projects), and pericyclic reactions features the most frequently. A lot of lithiation reactions and ring expansions / contractions as well.
Title: Re: reaction to know for total synthesis
Post by: OrganicDan96 on February 09, 2019, 02:51:37 PM: palladium couplings, suzuki, heck, nigishi stilli ect. not so much a reaction but protecting group chemistry is very useful as well.