Macrocycle

macrocyclicmacrocyclesmacrocyclizationmacrocyclic compoundsmacrocyclic chemistryfused ringmacrocyclic compoundmacrocyclic ligandmacrocyclic ligandsmacrocyclic molecules
Macrocycles are often described as molecules and ions containing twelve or more membered ring.wikipedia
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Calixarene

calixarenescalix[4]pyrrolesp''-''tert''-butyl[calix[6]arene macrocycle
Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins.
A calixarene is a macrocycle or cyclic oligomer based on a hydroxyalkylation product of a phenol and an aldehyde.

Porphyrin

porphyrinscoproporphyrinuroporphyrin
Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Many metallocofactors are bound to macrocyclic ligands, which include porphyrins, corrins, and chlorins.
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−).

Cyclodextrin

cyclodextrinsbeta-cyclodextrinβ-cyclodextrin
Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins.
Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds.

Macrolide

macrolidesmacrolide antibioticmacrolide antibiotics
One important application are the many macrocyclic antibiotics, the macrolides, e.g. vancomycin.
The macrolides are a class of natural products that consist of a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached.

High Dilution Principle

high-dilution reaction
This kinetic problem can be addressed by using high-dilution reactions, whereby intramolecular processes are favored relative to polymerizations.
In organic chemistry, the High Dilution Principle is a strategy for some macrocyclization reactions, i.e. the synthesis of macrocycles.

Corrin

corrin ringprecorrin-8x
Many metallocofactors are bound to macrocyclic ligands, which include porphyrins, corrins, and chlorins.
It is the parent macrocycle related to the substituted derivative that is found in vitamin B 12.

Muscone

Muscenone
An illustrative macrocyclization is the synthesis of -muscone from -citronellal.
A more recent enantioselective synthesis involves an intramolecular aldol addition/dehydration reaction of a macrocyclic diketone.

Rotaxane

rotaxanespseudorotaxane
A rotaxane is a mechanically interlocked molecular architecture consisting of a "dumbbell shaped molecule" which is threaded through a "macrocycle" (see graphical representation).

Catenane

catenanescatenated
A catenane is a mechanically-interlocked molecular architecture consisting of two or more interlocked macrocycles, i.e. a molecule containing two or more intertwined rings.

Macrocyclic stereocontrol

Macrocyclic stereocontrol models the substitution and reactions of medium and large rings in organic chemistry, with remote stereogenic elements providing enough conformational influence to direct the outcome of a reaction.

Crown ether

crown ethers
Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins.

Terpenoid

isoprenoidterpenoidsisoprenoids
Pioneering work was reported for studies on terpenoid macrocycles.

Template reaction

template effecttemplate reactionsTemplated
Some macrocyclizations are favored using template reactions.

Citronellal

(+)-citronellal(–)-(''S'')-citronellalrhodinal
An illustrative macrocyclization is the synthesis of -muscone from -citronellal.

Ring-closing metathesis

RCMring closure metathesisring-closing olefin metathesis
The 15-membered ring is generated by ring-closing metathesis.

Vancomycin

Red man syndromeRed man syndrome (Drug eruption)Vancocin
One important application are the many macrocyclic antibiotics, the macrolides, e.g. vancomycin.

Chlorin

bacteriochlorinchlorin groupisobacteriochlorin
Many metallocofactors are bound to macrocyclic ligands, which include porphyrins, corrins, and chlorins.

Ion transporter

ion transportion pumpion transporter (IT) superfamily
Macrocycles often bind ions and facilitate ion transport across hydrophobic membranes and solvents.

Phase-transfer catalyst

phase transfer catalystphase-transfer catalysisphase transfer catalysis
The macrocycle envelops the ion with a hydrophobic sheath, which facilitates phase transfer properties.

Cucurbituril

Cucurbiturils are macrocyclic molecules made of glycoluril (=C 4 H 2 N 4 O 2 =) monomers linked by methylene bridges (-CH 2 -).

Cyclen

1,4,7,10-tetraazacyclododecaneaza crown
Cyclen (1,4,7,10-tetraazacyclododecane) is a macrocycle and the aza analog of the crown ether 12-crown-4.

Resorcinarene

resorcinarenes
A resorcinarene (also resorcarene or calix[4]resorcinarene) is a macrocycle, or a cyclic oligomer, based on the condensation of resorcinol (1,3-dihydroxybenzene) and an aldehyde.