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- Carpanone abstract "Carpanone is a naturally occurring lignan-type natural product most widely known for the remarkably complex way nature prepares it, and the similarly remarkable success that an early chemistry group, that of Orville L. Chapman, had at mimicking nature's pathway. Carpanone is an organic compound first isolated from the carpano trees (Cinnamomum sp.) of Bougainville Island by Brophy and coworkers, trees from which the natural product derives its name. The hexacyclic lignan is one of a class of related diastereomers isolated from carpano bark as mixtures of equal proportion of the \"handedness\" of its components (i.e., racemic mixtures), and is notable in its stereochemical complexity, because it contains five contiguous stereogenic centers. The route by which this complex structure is achieved through biosynthesis involves a series of reactions that, almost instantly, take a molecule with little three-dimensionality to the complex final structure. Notably, Brophy and coworkers isolated the simpler carpacin, a phenylpropanoid with a 9-carbon framework, recognized its substructure as being dimerized within the complex carpanone structure, and proposed an hypothesis of how carpacin was converted to carpanone in plant cells: carpacin underwent loss of a methyl (-CH3) group from the ring methoxy (-OCH3) group to provide the phenol, desmethylcarpacin, this phenol intermediate then underwent a phenolic coupling to generate a dimeric intermediate, which was followed immediately by a Diels-Alder (4+2) cycloaddition reaction to create 2 new rings, to give the final carpanone product. Remarkably, within two years, Chapman and coworkers were able to chemically design a route to mimic this proposed biosynthetic route, and achieved the synthesis of carpanone from carpacin in a single \"pot\", in about 50% yield.Carpanone itself is limited in its pharmacologic and biologic activities, but related analogs arrived at by variations of the Brophy-Chapman approach have shown activities as tool compounds relevant to mammalian exocytosis and vesicular traffic, and provided therapeutic \"hits\" in antiinfective, antihypertensive, and hepatoprotective areas.The original Chapman design and synthesis is considered a classic in total synthesis, and one that highlights the power of biomimetic synthesis.".
- Carpanone thumbnail Carpanone.png?width=300.
- Carpanone wikiPageID "22792515".
- Carpanone wikiPageLength "11439".
- Carpanone wikiPageOutDegree "41".
- Carpanone wikiPageRevisionID "695666025".
- Carpanone wikiPageWikiLink Alkene.
- Carpanone wikiPageWikiLink Allyl.
- Carpanone wikiPageWikiLink Biomimetic_synthesis.
- Carpanone wikiPageWikiLink Biosynthesis.
- Carpanone wikiPageWikiLink Bougainville_Island.
- Carpanone wikiPageWikiLink Carpacin.
- Carpanone wikiPageWikiLink Cascade_reaction.
- Carpanone wikiPageWikiLink Category:Benzodioxoles.
- Carpanone wikiPageWikiLink Category:Ketones.
- Carpanone wikiPageWikiLink Category:Lignans.
- Carpanone wikiPageWikiLink Category:Total_synthesis.
- Carpanone wikiPageWikiLink Chirality.
- Carpanone wikiPageWikiLink Chirality_(chemistry).
- Carpanone wikiPageWikiLink Cinnamomum.
- Carpanone wikiPageWikiLink Claisen_rearrangement.
- Carpanone wikiPageWikiLink Cycloaddition.
- Carpanone wikiPageWikiLink Desmethyl.
- Carpanone wikiPageWikiLink Diastereomer.
- Carpanone wikiPageWikiLink Diels–Alder_reaction.
- Carpanone wikiPageWikiLink Enol.
- Carpanone wikiPageWikiLink Enone.
- Carpanone wikiPageWikiLink Hit_to_lead.
- Carpanone wikiPageWikiLink Lignan.
- Carpanone wikiPageWikiLink Natural_product.
- Carpanone wikiPageWikiLink Organic_compound.
- Carpanone wikiPageWikiLink Phenol.
- Carpanone wikiPageWikiLink Phenylpropanoid.
- Carpanone wikiPageWikiLink Quinone_methide.
- Carpanone wikiPageWikiLink Racemic_mixture.
- Carpanone wikiPageWikiLink Sesamol.
- Carpanone wikiPageWikiLink Total_synthesis.
- Carpanone wikiPageWikiLink X-ray_crystallography.
- Carpanone wikiPageWikiLink File:Carpacin.png.
- Carpanone wikiPageWikiLink File:Carpanone_synthesis.png.
- Carpanone wikiPageWikiLinkText "Carpanone".
- Carpanone wikiPageWikiLinkText "carpanone".
- Carpanone imagefile "Carpanone.png".
- Carpanone othernames "Cupanone".
- Carpanone verifiedrevid "402550745".
- Carpanone watchedfields "changed".
- Carpanone wikiPageUsesTemplate Template:Cascite.
- Carpanone wikiPageUsesTemplate Template:Chembox.
- Carpanone wikiPageUsesTemplate Template:Chembox_Hazards.
- Carpanone wikiPageUsesTemplate Template:Chembox_Identifiers.
- Carpanone wikiPageUsesTemplate Template:Chembox_Properties.
- Carpanone wikiPageUsesTemplate Template:Chemspidercite.
- Carpanone wikiPageUsesTemplate Template:Reflist.
- Carpanone wikiPageUsesTemplate Template:Stdinchicite.
- Carpanone subject Category:Benzodioxoles.
- Carpanone subject Category:Ketones.
- Carpanone subject Category:Lignans.
- Carpanone subject Category:Total_synthesis.
- Carpanone type ChemicalCompound.
- Carpanone type ChemicalSubstance.
- Carpanone type Group.
- Carpanone type Acetal.
- Carpanone type Ether.
- Carpanone type Group.
- Carpanone type Heterocycle.
- Carpanone type Ketone.
- Carpanone type Lignan.
- Carpanone type Phenylpropanoid.
- Carpanone type ChemicalObject.
- Carpanone type Thing.
- Carpanone type Q11173.
- Carpanone comment "Carpanone is a naturally occurring lignan-type natural product most widely known for the remarkably complex way nature prepares it, and the similarly remarkable success that an early chemistry group, that of Orville L. Chapman, had at mimicking nature's pathway. Carpanone is an organic compound first isolated from the carpano trees (Cinnamomum sp.) of Bougainville Island by Brophy and coworkers, trees from which the natural product derives its name.".
- Carpanone label "Carpanone".
- Carpanone sameAs Q5045601.
- Carpanone sameAs m.063_ks7.
- Carpanone sameAs Karpanon.
- Carpanone sameAs Karpanon.
- Carpanone sameAs Q5045601.
- Carpanone wasDerivedFrom Carpanone?oldid=695666025.
- Carpanone depiction Carpanone.png.
- Carpanone isPrimaryTopicOf Carpanone.