December 07, 2022, 02:37:16 AM
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Topic: Looking for a synthesis that employs some heteroatom chemistry  (Read 470 times)

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Offline AwkwardTsunami

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Looking for a synthesis that employs some heteroatom chemistry
« on: October 24, 2022, 10:06:46 AM »
I am looking for an organic synthesis (published) that utilises heteroatom chemistry. It is a mini project where I must describe a synthesis involving as much heteroatom chemistry as possible, in particular the following:
  • Hydroboration with 9-BBN, carbonylation of organoboranes, vinyl boronic acids
  • Silicone α and β effect, silyl protecting groups, nucleophilic attack on silicone, Si-F chemistry, vinyl silanes
  • TMS, TES, TBS, TIPS, TBDPS
  • Peterson olefination
  • Wittig reaction, Schlosser's modification of the Wittig reaction, Arbusov reaction
  • Horner-Wadsworth-Emmons reaction
  • Stille-Genari and Ando reactions; Corey-Fuchs reaction; Seyferth-Gilbert and Bestmann-Ohira reagent
  • Criege ozonolysis
  • Mitsunobu reaction, Appel reaction
  • Ramberg-Bäcklund reaction
  • Julia and Julia-Kocienski olefination
An adequate synthesis would include three or four of the above processes, with variety in the heteroatom of choice (so three consecutive reactions that only employ silyl chemistry would not be suitable). The product must also be "useful" in some capacity: whether biologically, or simply as an intermediate in another reaction is unimportant, but it must be something that can be described in layman's terms without too much additional research.

I understand that this is a long list, which is why this is quite an overwhelming task. I have looked at resources listing syntheses, such as https://organicchemistrydata.org/hansreich/resources/syntheses/?page=abscisic-acid-constantino%2F, and have found a few examples which are vaguely suitable, but none that fit all the criteria. For example: the synthesis of dihydroxanthatin found here https://pubs.acs.org/doi/10.1021/ol051276k or https://organicchemistrydata.org/hansreich/resources/syntheses/?page=xanthatin-dihydro-evans%2F has some organosilicon chemistry, but the Claisen condensation wouldn't come under the phosphorous chemistry we have studied (as far as I can tell). The CBS reduction is also an example of borane chemistry, but does not fall under the syllabus for this year, so I doubt it would fly.

Tl;dr: I am looking for a multiple step synthesis that involves some silicon, sulphur, phosphorous, and/or boron heteroatom chemistry. Ideally it contains three or more reactions from the above list, with variety in the heteroatom involved, and the use of the product can be described in layman's terms. It's a pretty tall order, so please let me know how I can better help people help me. I don't need an explanation of the synthesis, as I want the explanation to be my own, just a link to it published somewhere.

This is also my first post here, and whilst I have read the rules, please let me know if anything I have said is not appropriate for this forum or board. Thank you!

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