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.
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 ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.