Corey–Nicolaou macrolactonization
E466669
Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Corey–Nicolaou macrolactonization canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4741219 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Corey–Nicolaou macrolactonization Context triple: [E. J. Corey, developedMethod, Corey–Nicolaou macrolactonization]
-
A.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
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B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
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C.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
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D.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
-
E.
Trost asymmetric allylic alkylation
Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Corey–Nicolaou macrolactonization Target entity description: Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
-
A.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
C.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
-
D.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
-
E.
Trost asymmetric allylic alkylation
Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
- F. None of above. chosen
Statements (43)
| Predicate | Object |
|---|---|
| instanceOf |
macrolactonization reaction
ⓘ
named reaction ⓘ organic reaction ⓘ |
| advantage |
applicable to sensitive functional groups
ⓘ
high chemoselectivity for intramolecular lactonization ⓘ useful for large-ring formation ⓘ |
| bondsFormed |
ester bond
ⓘ
lactone C–O bond ⓘ |
| category |
Corey reactions
NERFINISHED
ⓘ
lactonization reactions ⓘ |
| developedBy |
Elias James Corey
NERFINISHED
ⓘ
K. C. Nicolaou NERFINISHED ⓘ |
| field |
natural product synthesis
ⓘ
organic synthesis ⓘ |
| formsProduct |
large-ring lactone
ⓘ
macrolactone ⓘ |
| limitation |
can compete with intermolecular esterification at high concentration
ⓘ
requires preorganization of hydroxy acid chain ⓘ |
| mechanisticFeature |
activated ester intermediate
ⓘ
intramolecular esterification ⓘ |
| namedAfter |
Elias James Corey
NERFINISHED
ⓘ
K. C. Nicolaou NERFINISHED ⓘ |
| reactionClass |
esterification
ⓘ
ring-closing reaction ⓘ |
| reactionOutcome | ring-closure with loss of small molecule byproduct ⓘ |
| reactionType |
lactonization
ⓘ
macrocyclization ⓘ |
| relatedTo |
Mitsunobu macrolactonization
NERFINISHED
ⓘ
Yamaguchi macrolactonization NERFINISHED ⓘ |
| ringSize | macrocyclic ring ⓘ |
| selectivity | favors intramolecular over intermolecular ester formation ⓘ |
| startingMaterial |
hydroxy acid
ⓘ
ω-hydroxy carboxylic acid ⓘ |
| substrateScope |
primary alcohol-containing hydroxy acids
ⓘ
secondary alcohol-containing hydroxy acids ⓘ |
| transformation | converts hydroxy acid to macrocyclic ester ⓘ |
| typicalCondition |
dehydrative cyclization
ⓘ
high-dilution conditions ⓘ |
| typicalRingSize | 12- to 30-membered ring ⓘ |
| usedFor |
formation of macrocyclic lactones under mild conditions
ⓘ
synthesis of macrocyclic natural products ⓘ |
| usedIn |
total synthesis of macrocyclic polyketides
ⓘ
total synthesis of macrolide antibiotics ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
Instruction
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Input
Subject: Corey–Nicolaou macrolactonization Description of subject: Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.