Matches in SemOpenAlex for { <https://semopenalex.org/work/W2076171454> ?p ?o ?g. }
Showing items 1 to 72 of
72
with 100 items per page.
- W2076171454 endingPage "185" @default.
- W2076171454 startingPage "173" @default.
- W2076171454 abstract "Zinc iodide catalyzed cycloaddition of furan to 1-cyanovinyl (1′S)-camphanate or 1-cyanovinyl (1′R)-camphanate led to optically pure (1R,2S,4R)-2-exo-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1′S)-camphanate and (1S,2R,4S)-2-exo-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1′R)-camphanate, respectively. Saponification afforded (1R,4R)- and (1S,4S)-7-oxabicyclo[2.2.1]hept-5-en-2-one, respectively, allowing concurrent recovery of the chiral auxiliaries, (1S)- and (1R)-camphanic acid, respectively. The 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (naked sugars) so obtained can be substituted at C(3), C(5) and C(6) by direct techniques with high stereoselectivity. The methods exploit the exo-facial selectivity of the reactions of these bicyclic systems and the regiochemical control exerted by the remote substituents at C(2) in electrophilic attack at C(5) and C(6). The polysubstituted 7-oxabicyclo[2.2.1]heptan-2-ones so obtained are chirons that can be converted into D- or L-hexose derivatives and analogues, into 2,5-anhydrohexonic acid derivatives (precursors for C-nucleosides and C-glycosides), or into polysubstituted 2-cyclohexen-1-ones. Moreover, conditions have been found under which the bicyclic ethers can be rearranged stereoselectively into polysubstituted cyclopentane-carbaldehydes. Compared with natural carbohydrates, the naked sugars are chirons with the following advantages: (1) the problem of selective protection and deprotection of polyalcoholic systems does not exist; (2) the functional moieties are grafted sequentially onto C(3), C(5), and C(6) of the 7-oxabicyclo[2.2.1]heptane systems together with the appropriate protective groups; (3) since both enantiomeric forms of the naked sugars are available, either enantiomer of a target compound can be reached with equal ease. 1. Introduction 2. The Carbonyl Group as Homoconjugated Electron-Releasing Substituent 3. Total Synthesis of 2,5-Anhydro-3-deoxy- and -4-deoxy-D-hexonic Acids and Related Deoxyadenosines-C 4. Total Syntheses of ribo-C-Nuleosides 5. De Novo Syntheses of D- and L-Hexoses and Analogues 6. Acid-Catalyzed Rearrangements of 5-exo-6-exo-Epoxy-7-oxa-2-norbornyl Derivatives 7. Stereoselective trans-Amino-hydroxylation of 7-Oxa-5-norbornen-2-one 8. The 7-Oxa-2-norbornanone/2-Cyclohexen-1-one Rearrangement: Total Syntheses of Conduritols 9. Conclusion and Perspectives" @default.
- W2076171454 created "2016-06-24" @default.
- W2076171454 creator A5032192926 @default.
- W2076171454 creator A5059812669 @default.
- W2076171454 creator A5082026323 @default.
- W2076171454 creator A5087361577 @default.
- W2076171454 date "1990-01-01" @default.
- W2076171454 modified "2023-10-15" @default.
- W2076171454 title "Optically Pure 7-Oxabicyclo[2.2.1]hept-5-en-2-yl Derivatives (Naked Sugars) as New Chirons" @default.
- W2076171454 doi "https://doi.org/10.1055/s-1990-21027" @default.
- W2076171454 hasPublicationYear "1990" @default.
- W2076171454 type Work @default.
- W2076171454 sameAs 2076171454 @default.
- W2076171454 citedByCount "143" @default.
- W2076171454 countsByYear W20761714542012 @default.
- W2076171454 countsByYear W20761714542013 @default.
- W2076171454 countsByYear W20761714542014 @default.
- W2076171454 countsByYear W20761714542015 @default.
- W2076171454 countsByYear W20761714542016 @default.
- W2076171454 countsByYear W20761714542017 @default.
- W2076171454 countsByYear W20761714542019 @default.
- W2076171454 countsByYear W20761714542021 @default.
- W2076171454 crossrefType "journal-article" @default.
- W2076171454 hasAuthorship W2076171454A5032192926 @default.
- W2076171454 hasAuthorship W2076171454A5059812669 @default.
- W2076171454 hasAuthorship W2076171454A5082026323 @default.
- W2076171454 hasAuthorship W2076171454A5087361577 @default.
- W2076171454 hasConcept C118792377 @default.
- W2076171454 hasConcept C155647269 @default.
- W2076171454 hasConcept C161790260 @default.
- W2076171454 hasConcept C178790620 @default.
- W2076171454 hasConcept C181647583 @default.
- W2076171454 hasConcept C185592680 @default.
- W2076171454 hasConcept C24961977 @default.
- W2076171454 hasConcept C2777052750 @default.
- W2076171454 hasConcept C2778659115 @default.
- W2076171454 hasConcept C2779664164 @default.
- W2076171454 hasConcept C50027330 @default.
- W2076171454 hasConcept C71240020 @default.
- W2076171454 hasConceptScore W2076171454C118792377 @default.
- W2076171454 hasConceptScore W2076171454C155647269 @default.
- W2076171454 hasConceptScore W2076171454C161790260 @default.
- W2076171454 hasConceptScore W2076171454C178790620 @default.
- W2076171454 hasConceptScore W2076171454C181647583 @default.
- W2076171454 hasConceptScore W2076171454C185592680 @default.
- W2076171454 hasConceptScore W2076171454C24961977 @default.
- W2076171454 hasConceptScore W2076171454C2777052750 @default.
- W2076171454 hasConceptScore W2076171454C2778659115 @default.
- W2076171454 hasConceptScore W2076171454C2779664164 @default.
- W2076171454 hasConceptScore W2076171454C50027330 @default.
- W2076171454 hasConceptScore W2076171454C71240020 @default.
- W2076171454 hasIssue "04" @default.
- W2076171454 hasLocation W20761714541 @default.
- W2076171454 hasOpenAccess W2076171454 @default.
- W2076171454 hasPrimaryLocation W20761714541 @default.
- W2076171454 hasRelatedWork W1972189081 @default.
- W2076171454 hasRelatedWork W2012047107 @default.
- W2076171454 hasRelatedWork W2065064409 @default.
- W2076171454 hasRelatedWork W2115218701 @default.
- W2076171454 hasRelatedWork W2734047078 @default.
- W2076171454 hasRelatedWork W2949761939 @default.
- W2076171454 hasRelatedWork W3184430197 @default.
- W2076171454 hasRelatedWork W4206560091 @default.
- W2076171454 hasRelatedWork W4244387284 @default.
- W2076171454 hasRelatedWork W4306970969 @default.
- W2076171454 hasVolume "1990" @default.
- W2076171454 isParatext "false" @default.
- W2076171454 isRetracted "false" @default.
- W2076171454 magId "2076171454" @default.
- W2076171454 workType "article" @default.