April 21, 2019, 04:29:48 AM
Forum Rules: Read This Before Posting


Topic: reaction to know for total synthesis  (Read 1013 times)

0 Members and 1 Guest are viewing this topic.

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1301
  • Mole Snacks: +107/-15
reaction to know for total synthesis
« 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

Offline OrganicDan96

  • Full Member
  • ****
  • Posts: 146
  • Mole Snacks: +10/-0
Re: reaction to know for total synthesis
« Reply #1 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

Offline wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 1192
  • Mole Snacks: +136/-9
Re: reaction to know for total synthesis
« Reply #2 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.

Offline hypervalent_iodine

  • Chemist
  • Full Member
  • *
  • Posts: 169
  • Mole Snacks: +23/-1
Re: reaction to know for total synthesis
« Reply #3 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.

Offline phth

  • Chemist
  • Full Member
  • *
  • Posts: 432
  • Mole Snacks: +32/-4
Re: reaction to know for total synthesis
« Reply #4 on: January 26, 2019, 12:28:30 AM »
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.

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1301
  • Mole Snacks: +107/-15
Re: reaction to know for total synthesis
« Reply #5 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.

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 3641
  • Mole Snacks: +234/-16
Re: reaction to know for total synthesis
« Reply #6 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.

Offline wildfyr

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 1192
  • Mole Snacks: +136/-9
Re: reaction to know for total synthesis
« Reply #7 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.

Offline hypervalent_iodine

  • Chemist
  • Full Member
  • *
  • Posts: 169
  • Mole Snacks: +23/-1
Re: reaction to know for total synthesis
« Reply #8 on: February 06, 2019, 01:18:44 AM »
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.

Offline OrganicDan96

  • Full Member
  • ****
  • Posts: 146
  • Mole Snacks: +10/-0
Re: reaction to know for total synthesis
« Reply #9 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.

Sponsored Links