Matches in SemOpenAlex for { <https://semopenalex.org/work/W1988162105> ?p ?o ?g. }
- W1988162105 endingPage "3270" @default.
- W1988162105 startingPage "3263" @default.
- W1988162105 abstract "4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp(2)ZrBu(2), followed by treatment with MeMgBr and then O(2), gave 2a in 63% yield by a one-pot reaction, since the approach of O(2) to zirconium was prevented by the aryl group. The total syntheses of (+/-)-mesembrane and (+/-)-mesembrine were achieved starting from 2a. To synthesize these natural products in a chiral form, the starting allylamine derivative 24 (80% yield, 86% ee, recrystallized from MeOH, 99% ee with 79% recovery) was prepared from allyl carbonate 22a and N-tosylallylamine 23 using palladium-catalyzed asymmetric amination in the presence of (S)-BINAPO as a chiral ligand. (-)-Mesembrane and (-)-mesembrine were synthesized from this allylamine 24." @default.
- W1988162105 created "2016-06-24" @default.
- W1988162105 creator A5005663108 @default.
- W1988162105 creator A5028753933 @default.
- W1988162105 creator A5042809348 @default.
- W1988162105 creator A5080057116 @default.
- W1988162105 date "1997-05-01" @default.
- W1988162105 modified "2023-10-17" @default.
- W1988162105 title "Total Syntheses of (−)-Mesembrane and (−)-Mesembrine via Palladium-Catalyzed Enantioselective Allylic Substitution and Zirconium-Promoted Cyclization" @default.
- W1988162105 cites W1974992646 @default.
- W1988162105 cites W1978890358 @default.
- W1988162105 cites W1980693907 @default.
- W1988162105 cites W1981296228 @default.
- W1988162105 cites W1982827268 @default.
- W1988162105 cites W1987624533 @default.
- W1988162105 cites W1989058130 @default.
- W1988162105 cites W1993714570 @default.
- W1988162105 cites W2011996195 @default.
- W1988162105 cites W2015664863 @default.
- W1988162105 cites W2037172987 @default.
- W1988162105 cites W2041348337 @default.
- W1988162105 cites W2048109065 @default.
- W1988162105 cites W2052527347 @default.
- W1988162105 cites W2073276601 @default.
- W1988162105 cites W2082630382 @default.
- W1988162105 cites W2119110063 @default.
- W1988162105 cites W2119580313 @default.
- W1988162105 cites W2143435135 @default.
- W1988162105 cites W2949403669 @default.
- W1988162105 cites W2949410973 @default.
- W1988162105 cites W2950155505 @default.
- W1988162105 cites W2950401958 @default.
- W1988162105 cites W2950598898 @default.
- W1988162105 cites W2950612890 @default.
- W1988162105 cites W2950714524 @default.
- W1988162105 cites W2951037197 @default.
- W1988162105 cites W2951099745 @default.
- W1988162105 cites W2951406263 @default.
- W1988162105 cites W2951584219 @default.
- W1988162105 cites W4231375801 @default.
- W1988162105 doi "https://doi.org/10.1021/jo9701187" @default.
- W1988162105 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11671713" @default.
- W1988162105 hasPublicationYear "1997" @default.
- W1988162105 type Work @default.
- W1988162105 sameAs 1988162105 @default.
- W1988162105 citedByCount "84" @default.
- W1988162105 countsByYear W19881621052012 @default.
- W1988162105 countsByYear W19881621052013 @default.
- W1988162105 countsByYear W19881621052014 @default.
- W1988162105 countsByYear W19881621052015 @default.
- W1988162105 countsByYear W19881621052016 @default.
- W1988162105 countsByYear W19881621052017 @default.
- W1988162105 countsByYear W19881621052018 @default.
- W1988162105 countsByYear W19881621052019 @default.
- W1988162105 countsByYear W19881621052020 @default.
- W1988162105 crossrefType "journal-article" @default.
- W1988162105 hasAuthorship W1988162105A5005663108 @default.
- W1988162105 hasAuthorship W1988162105A5028753933 @default.
- W1988162105 hasAuthorship W1988162105A5042809348 @default.
- W1988162105 hasAuthorship W1988162105A5080057116 @default.
- W1988162105 hasConcept C116569031 @default.
- W1988162105 hasConcept C120095180 @default.
- W1988162105 hasConcept C134121241 @default.
- W1988162105 hasConcept C146686406 @default.
- W1988162105 hasConcept C153356533 @default.
- W1988162105 hasConcept C155647269 @default.
- W1988162105 hasConcept C161790260 @default.
- W1988162105 hasConcept C170493617 @default.
- W1988162105 hasConcept C178790620 @default.
- W1988162105 hasConcept C185592680 @default.
- W1988162105 hasConcept C188027245 @default.
- W1988162105 hasConcept C191897082 @default.
- W1988162105 hasConcept C192562407 @default.
- W1988162105 hasConcept C198503264 @default.
- W1988162105 hasConcept C2778927588 @default.
- W1988162105 hasConcept C2780263894 @default.
- W1988162105 hasConcept C2781076698 @default.
- W1988162105 hasConcept C502130503 @default.
- W1988162105 hasConcept C521977710 @default.
- W1988162105 hasConcept C534791751 @default.
- W1988162105 hasConcept C55493867 @default.
- W1988162105 hasConceptScore W1988162105C116569031 @default.
- W1988162105 hasConceptScore W1988162105C120095180 @default.
- W1988162105 hasConceptScore W1988162105C134121241 @default.
- W1988162105 hasConceptScore W1988162105C146686406 @default.
- W1988162105 hasConceptScore W1988162105C153356533 @default.
- W1988162105 hasConceptScore W1988162105C155647269 @default.
- W1988162105 hasConceptScore W1988162105C161790260 @default.
- W1988162105 hasConceptScore W1988162105C170493617 @default.
- W1988162105 hasConceptScore W1988162105C178790620 @default.
- W1988162105 hasConceptScore W1988162105C185592680 @default.
- W1988162105 hasConceptScore W1988162105C188027245 @default.
- W1988162105 hasConceptScore W1988162105C191897082 @default.
- W1988162105 hasConceptScore W1988162105C192562407 @default.
- W1988162105 hasConceptScore W1988162105C198503264 @default.
- W1988162105 hasConceptScore W1988162105C2778927588 @default.
- W1988162105 hasConceptScore W1988162105C2780263894 @default.
- W1988162105 hasConceptScore W1988162105C2781076698 @default.