FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2025931094> ?p ?o ?g. }

• W2025931094 endingPage "411" @default.
• W2025931094 startingPage "405" @default.
• W2025931094 abstract "Facile enantioselective syntheses of the di-O-methyl ethers of the norlignans, (–)-agatharesinol (–)-1a, (+)-hinokiresinol (+)-2a and (–)-sugiresinol (–)-3a are described. Grignard addition of vinylmagnesium bromide to an aldimine (–)-13, prepared from the tert-butyl ester 11 and 4-methoxycinnamaldehyde 12, afforded a homochiral vinyl aldehyde, (–)-3-(4-methoxyphenyl)pent-4-enal (–)-14 in >95% ee, which was converted into a diastereoisomeric mixture of 1,3-bis(4-methoxyphenyl)pent-4-en-1-ols (3R)-6 by a second Grignard reaction with 4-methoxyphenylmagnesium bromide. Sharpless' asymmetric dihydroxylation of the vinyl alcohols (3R)-6 proceeded diastereoselectively to give the triol of desired relative stereochemistry (2S,3S)-7. This, upon dehydration, afforded (–)-di-O-methylsugiresinol (–)-3b, the subsequent acid-catalysed cyclization of which gave (–)-di-O-methyl agatharesinol (–)-1b. (+)-Di-O-methylhinokiresinol (+)-2b was readily obtained by the dehydration of the vinyl alcohols (3R)-6." @default.
• W2025931094 created "2016-06-24" @default.
• W2025931094 creator A5002610788 @default.
• W2025931094 creator A5057013161 @default.
• W2025931094 creator A5060022860 @default.
• W2025931094 creator A5067180371 @default.
• W2025931094 date "1996-01-01" @default.
• W2025931094 modified "2023-10-09" @default.
• W2025931094 title "Enantioselective total synthesis of the di-O-methyl ethers of (–)-agatharesinol, (+)-hinokiresinol and (–)-sugiresinol, characteristic norlignans of Coniferae" @default.
• W2025931094 cites W1491711308 @default.
• W2025931094 cites W1603350078 @default.
• W2025931094 cites W1969797964 @default.
• W2025931094 cites W1972139427 @default.
• W2025931094 cites W1973563264 @default.
• W2025931094 cites W1975361019 @default.
• W2025931094 cites W1976747105 @default.
• W2025931094 cites W1980806858 @default.
• W2025931094 cites W1981633196 @default.
• W2025931094 cites W1988040765 @default.
• W2025931094 cites W1996798433 @default.
• W2025931094 cites W2002886759 @default.
• W2025931094 cites W2012171927 @default.
• W2025931094 cites W2019691443 @default.
• W2025931094 cites W2019743900 @default.
• W2025931094 cites W2023884089 @default.
• W2025931094 cites W2027703301 @default.
• W2025931094 cites W2029835011 @default.
• W2025931094 cites W2035595625 @default.
• W2025931094 cites W2040766532 @default.
• W2025931094 cites W2043966259 @default.
• W2025931094 cites W2044811827 @default.
• W2025931094 cites W2044917570 @default.
• W2025931094 cites W2045025805 @default.
• W2025931094 cites W2064267898 @default.
• W2025931094 cites W2073074313 @default.
• W2025931094 cites W2080560091 @default.
• W2025931094 cites W2087090593 @default.
• W2025931094 cites W2087723892 @default.
• W2025931094 cites W2137534575 @default.
• W2025931094 cites W2333046379 @default.
• W2025931094 cites W2952746512 @default.
• W2025931094 cites W4243703356 @default.
• W2025931094 doi "https://doi.org/10.1039/p19960000405" @default.
• W2025931094 hasPublicationYear "1996" @default.
• W2025931094 type Work @default.
• W2025931094 sameAs 2025931094 @default.
• W2025931094 citedByCount "10" @default.
• W2025931094 countsByYear W20259310942017 @default.
• W2025931094 crossrefType "journal-article" @default.
• W2025931094 hasAuthorship W2025931094A5002610788 @default.
• W2025931094 hasAuthorship W2025931094A5057013161 @default.
• W2025931094 hasAuthorship W2025931094A5060022860 @default.
• W2025931094 hasAuthorship W2025931094A5067180371 @default.
• W2025931094 hasConcept C146686406 @default.
• W2025931094 hasConcept C155647269 @default.
• W2025931094 hasConcept C161790260 @default.
• W2025931094 hasConcept C178790620 @default.
• W2025931094 hasConcept C185592680 @default.
• W2025931094 hasConcept C2776300020 @default.
• W2025931094 hasConcept C2776626252 @default.
• W2025931094 hasConcept C2777672777 @default.
• W2025931094 hasConcept C2778769901 @default.
• W2025931094 hasConcept C2779144480 @default.
• W2025931094 hasConcept C2779515768 @default.
• W2025931094 hasConcept C2779825165 @default.
• W2025931094 hasConcept C2780616238 @default.
• W2025931094 hasConcept C2781306241 @default.
• W2025931094 hasConcept C40875361 @default.
• W2025931094 hasConcept C55493867 @default.
• W2025931094 hasConcept C71240020 @default.
• W2025931094 hasConceptScore W2025931094C146686406 @default.
• W2025931094 hasConceptScore W2025931094C155647269 @default.
• W2025931094 hasConceptScore W2025931094C161790260 @default.
• W2025931094 hasConceptScore W2025931094C178790620 @default.
• W2025931094 hasConceptScore W2025931094C185592680 @default.
• W2025931094 hasConceptScore W2025931094C2776300020 @default.
• W2025931094 hasConceptScore W2025931094C2776626252 @default.
• W2025931094 hasConceptScore W2025931094C2777672777 @default.
• W2025931094 hasConceptScore W2025931094C2778769901 @default.
• W2025931094 hasConceptScore W2025931094C2779144480 @default.
• W2025931094 hasConceptScore W2025931094C2779515768 @default.
• W2025931094 hasConceptScore W2025931094C2779825165 @default.
• W2025931094 hasConceptScore W2025931094C2780616238 @default.
• W2025931094 hasConceptScore W2025931094C2781306241 @default.
• W2025931094 hasConceptScore W2025931094C40875361 @default.
• W2025931094 hasConceptScore W2025931094C55493867 @default.
• W2025931094 hasConceptScore W2025931094C71240020 @default.
• W2025931094 hasIssue "5" @default.
• W2025931094 hasLocation W20259310941 @default.
• W2025931094 hasOpenAccess W2025931094 @default.
• W2025931094 hasPrimaryLocation W20259310941 @default.
• W2025931094 hasRelatedWork W1970830746 @default.
• W2025931094 hasRelatedWork W2015108788 @default.
• W2025931094 hasRelatedWork W2025931094 @default.
• W2025931094 hasRelatedWork W2173876110 @default.
• W2025931094 hasRelatedWork W2602751511 @default.
• W2025931094 hasRelatedWork W2610720782 @default.
• W2025931094 hasRelatedWork W2748166936 @default.

• next