@SynStrategy

SynStrategy categorizes 500+ reactions by the functional group they form. It contains 400+ total synthesis examples and is completely free for iOS and Android

synstrategy.org
Joined September 2022
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With the new semester, we released an update for @SynStrategy! We added mechanisms, beginning with some oxidation reactions. Building on our quiz & flashcard features, a new statistics tab lets you track completed quizzes and top-searched reactions. Free on iOS & Android!
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The Nierenstein reaction converts acyl chlorides into α-chloroketones using diazomethane. The presence of HCl prevents a competing Wolff rearrangement. The reaction has been applied in the #TotalSynthesis of (-)-Dysibetaine by Kobayashi and co-workers. References in thread!
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Reference for the #TotalSynthesis of (-)-Dysibetaine: onlinelibrary.wiley.com/doi/… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

An Ugi Reaction in the Total Synthesis of (−)‐Dysibetaine

(−)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts...

onlinelibrary.wiley.com
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The Finkelstein reaction converts alkyl halides or sulfonates into other halides via an SN2 exchange with corresponding halide salts. Overman & co-workers exchanged an -OMs for a chloride using LiCl in the #TotalSynthesis of (-)-Strychnine @UCIChemistry References in thread!
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Reference for the #TotalSynthesis of (-)-Strychnine: pubs.acs.org/jacsat/article-… Explore more reactions and their synthetic applications and download the free app! synstrategy.org #Chemistry

Synthesis applications of cationic aza-Cope rearrangements. 26. Enantioselective total synthesis of...

Steven D. Knight, Larry E. Overman, Garry Pairaudeau; Synthesis applications of cationic aza-Cope rearrangements. 26. Enantioselective total synthesis of (

pubs.acs.org
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The Hofmann elimination generates alkenes from quaternary ammonium salts when treated with base, expelling an amine. The reaction has been applied in the #TotalSynthesis of (-)-Quinine by Woodward and co-workers @HarvardCCB to generate a terminal alkene. References in thread!
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Reference for the #TotalSynthesis of (-)-Quinine: pubs.acs.org/jacsat/article-… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

The Total Synthesis of Quinine

R. B. Woodward, W. E. Doering; The Total Synthesis of Quinine, Journal of the American Chemical Society, Volume 67, Issue 5, 1 May 1945, Pages 860–874, htt

pubs.acs.org
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In the DeMayo reaction, the enol of a 1,3-dicarbonyl and an alkene undergo [2+2] cycloaddition. Retro-aldol of the resulting cyclobutanol yields a 1,5-dicarbonyl. This has been applied in the #TotalSynthesis of (±)-Longifolene by Oppolzer & co-workers. References in thread!
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Reference for the #TotalSynthesis of (±)-Longifolene: pubs.acs.org/jacsat/article-… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

A new and efficient total synthesis of (.+-.)-longifolene

Wolfgang Oppolzer, Thierry Godel; A new and efficient total synthesis of (.+-.)-longifolene, Journal of the American Chemical Society, Volume 100, Issue 8,

pubs.acs.org
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In the Reformatsky reaction, an α-halo ester is treated with zinc to form an organozinc reagent that adds to carbonyls, yielding β-hydroxy esters. The reaction was applied in the #TotalSynthesis of (−)-Artemisinin by Giannis and co-workers. References in thread!
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Reference for the #TotalSynthesis of (−)-Artemisinin: onlinelibrary.wiley.com/doi/… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

Total Synthesis and Biological Investigation of (−)‐Artemisinin: The Antimalarial Activity of...

Mirror, mirror on the wall, who is the most active one of all? Both (−)- and (+)-artemisinin were synthesized biomimetically and their activity was tested against the malaria parasite Plasmodium...

onlinelibrary.wiley.com
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The Johnson iodination converts an α,β-unsaturated carbonyl into an α-iodoenone by treating the substrate with iodine and DMAP. This reaction has been applied in the #TotalSynthesis of (−)-Curcusone A by Mingji Dai and co-workers. References in thread!
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Reference for the #TotalSynthesis of (−)-Curcusone A: pubs.acs.org/jacsat/article-… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

Total Synthesis and Target Identification of the Curcusone Diterpenes

Abstract. The curcusone natural products are complex diterpenes featuring a characteristic [6–7–5] tricyclic carbon skeleton similar to the daphnane and ti

pubs.acs.org
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Download or update the app here for the new semester: synstrategy.org

SynStrategy - Organic Chemistry App by Functional Group

Organic reactions categorized by the functional group they form. 500+ transformations, 400+ total synthesis examples, custom datasets, quizzes and flashcards.

synstrategy.org
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The Paal-Knorr pyrrole synthesis is a condensation reaction between a 1,4-dicarbonyl and an amine to form pyrroles. In the #TotalSynthesis of (±)-Marinopyrrole B by Clive and co-workers, the amine was added in the form of ammonium acetate. References in thread!
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Reference for the #TotalSynthesis of (±)-Marinopyrrole B: pubs.rsc.org/cc/article-abst… Explore more reactions and their synthetic applications and download the free app! synstrategy.org

Racemic marinopyrrole B by total synthesis†

The first synthesis of marinopyrrole B, which is highly active against methicillin-resistant Staphylococcus aureus, is described. The route involved constr

pubs.rsc.org
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The Kornblum oxidation uses DMSO and base to access aldehydes, ketones, and 1,2-dicarbonyls from alkyl or benzyl halides, or α-halo esters. The reaction was applied by Nicolaou and co-workers @RiceUniversity in the #TotalSynthesis of (–)-Halichondrin B. References in thread!
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Reference for the #TotalSynthesis of (–)-Halichondrin B: pubs.acs.org/jacsat/article-… Explore more reactions and their synthetic applications and download the app! synstrategy.org

A Reverse Approach to the Total Synthesis of Halichondrin B

Abstract. A new strategy is described for the total synthesis of halichondrin B featuring reversal of the sequential construction of a number of its cyclic

pubs.acs.org
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The Neber #rearrangement generates α-amino ketones when oxime tosylates are treated with base. In the #TotalSynthesis of (+)-Dragmacidin F by @thestoltzgroup @CaltechCCE , the resulting α-amino ketone was elaborated into an aminoimidazole. References in thread!
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Reference for the #TotalSynthesis of (+)-Dragmacidin F: pubs.acs.org/doi/10.1021/ja0… Explore more reactions and their synthetic applications and download the app! synstrategy.org

The Total Synthesis of (+)-Dragmacidin F

Abstract. The first total synthesis of (+)-dragmacidin F has been accomplished, establishing the absolute configuration of this biologically important, ant

pubs.acs.org
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