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#ChemTwitter
Reference for the #TotalSynthesis of (+)-Brasilenyne:
https://t.co/BXnCWnYMcb
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The Brown asymmetric allylation/crotylation employs diisopinocampheylborane for the enantio- and diastereoselective synthesis of homoallylic alcohols.
The #reaction was applied by the Denmark group @ChemistryUIUC in the #TotalSynthesis of (+)-Brasilenyne.
References in thread!
Link to the #TotalSynthesis of (-)-Okilactomycin:
https://t.co/Q8Tqpdb8Dn
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The Petasis-Ferrier #rearrangement transforms vinyl acetals into β-hydroxy ketones in the presence of a Lewis acid. Cyclic substrates result in tetrahydropyranones, a strategy applied in the #TotalSynthesis of (-)-Okilactomycin by the Smith group.
Links in thread!
Link to the #TotalSynthesis of (-)-Taxol:
https://t.co/aplxdup1Q3
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In the Davis asymmetric oxidation, a chiral oxaziridine derived from camphorsulfonic acid enables the enantioselective α-hydroxylation of enolates.
The Holton group leveraged this #Reaction in the first #TotalSynthesis of #Taxol.
Links in thread!
The Semmler-Wolff #Reaction transforms α,β-unsaturated oximes into aniline derivatives under acidic conditions or heat.
This transformation was applied in the #TotalSynthesis of (-)-Penitrem D by the Smith group.
Links in thread!
Link to the #TotalSynthesis of (+)-Jasplakinolide:
https://t.co/KdlzUF5wcG
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The Arndt-Eistert homologation proceeds via a ketene intermediate to transform acid chlorides or anhydrides into homologated carboxylic acids, esters, or amides.
This method was utilized in the #TotalSynthesis of (+)-Jasplakinolide by the Grieco group.
Links in thread!
Link to the #TotalSynthesis of
(-)-Penitrem D:
https://t.co/GPJYWBqUo0
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Link to the #TotalSynthesis of (±)-Tirandamycin:
https://t.co/QhyE6YokIn
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The Achmatowicz reaction transforms a furyl alcohol into a dihydropyranone via an oxidative rearrangement using Br₂, NBS, or mCPBA.
This transformation was applied in the #TotalSynthesis of (±)-Tirandamycin by the DeShong group. Links in thread!
Link to the #TotalSynthesis of (+)-Neaumycin B:
https://t.co/gBmPnelJUm
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The Marshall propargylation is a palladium-catalyzed stereoselective addition of a propargyl group to an aldehyde, affording homopropargylic alcohols.
This method was utilized in the #TotalSynthesis of (+)-Neaumycin B by the Wang, Zhang, and Chen groups.
Links in thread!
Link to the #TotalSynthesis of (+)-Vulgarisin B: https://t.co/lCYqOBG9oR
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The [2,3]-Wittig rearrangement can occur when allylic ethers are treated with a strong base, transforming them into homoallylic alcohols.
An application was reported by the Ding Group in the #TotalSynthesis of (+)-Vulgarisin B. Links in thread!
Link to the #TotalSynthesis of (-)-Laulimalide: https://t.co/mnU2pqBAGn
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The Ohira-Bestmann reagent transforms aldehydes into terminal alkynes under mild conditions.
A notable application was reported by the Wender group ( @StanfordUChem ) in their #TotalSynthesis of (-)-Laulimalide.
Links in thread!
Link to the Total Synthesis of (-)-Azadirachtin: https://t.co/tq6WrhiEQB
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The Saucy-Marbet rearrangement: a [3,3]-sigmatropic shift
turning propargyl vinyl ethers into allenic carbonyls.
Notable Application: The total synthesis of (–)-Azadirachtin by the Ley group,
where it was used to construct a C-C bond between two fragments.
Link in 💬 below!