Matches in SemOpenAlex for { <https://semopenalex.org/work/W1988718750> ?p ?o ?g. }
- W1988718750 endingPage "3101" @default.
- W1988718750 startingPage "3093" @default.
- W1988718750 abstract "A novel and general method has been developed for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide-initiated cationic cyclization of azides. The key cyclization reaction was systematically studied with the model compound, 3-(1-oxa-spiro[2.4]hept-4-yl)propyl azide 3a, and EtAlCl2 was found to be an ideal choice as the catalyst. The generality of this transformation was further tested with different ring sizes, where six- and seven-membered epoxyazides 3b,c underwent smooth cyclization to give 5-hydroxymethyl azepine 4b and 5-hydroxymethyl azocine 4c, respectively, as a single detectable diastereomer. This novel methodology was elegantly applied in the stereoselective total synthesis of indolizidine alkaloids 167B and 209D. Further, the enantioselective total synthesis of natural and unnatural indolizidine alkaloids 167B and 209D was accomplished by using Sharpless asymmetric dihydroxylation as a key step." @default.
- W1988718750 created "2016-06-24" @default.
- W1988718750 creator A5049719312 @default.
- W1988718750 creator A5059031550 @default.
- W1988718750 date "2004-04-01" @default.
- W1988718750 modified "2023-09-25" @default.
- W1988718750 title "Epoxide-Initiated Cationic Cyclization of Azides: A Novel Method for the Stereoselective Construction of 5-Hydroxymethyl Azabicyclic Compounds and Application in the Stereo- and Enantioselective Total Synthesis of (+)- and (−)-Indolizidine 167B and 209D" @default.
- W1988718750 cites W1965421002 @default.
- W1988718750 cites W1965955431 @default.
- W1988718750 cites W1969355693 @default.
- W1988718750 cites W1971577960 @default.
- W1988718750 cites W1974422933 @default.
- W1988718750 cites W1974502783 @default.
- W1988718750 cites W1975915696 @default.
- W1988718750 cites W1989146433 @default.
- W1988718750 cites W1991075022 @default.
- W1988718750 cites W1992524260 @default.
- W1988718750 cites W2000428647 @default.
- W1988718750 cites W2001540676 @default.
- W1988718750 cites W2002003343 @default.
- W1988718750 cites W2006558878 @default.
- W1988718750 cites W2010009089 @default.
- W1988718750 cites W2024001994 @default.
- W1988718750 cites W2034556247 @default.
- W1988718750 cites W2037078725 @default.
- W1988718750 cites W2043077062 @default.
- W1988718750 cites W2045521774 @default.
- W1988718750 cites W2047490982 @default.
- W1988718750 cites W2048688736 @default.
- W1988718750 cites W2069321616 @default.
- W1988718750 cites W2070175622 @default.
- W1988718750 cites W2074687807 @default.
- W1988718750 cites W2076976947 @default.
- W1988718750 cites W2101275411 @default.
- W1988718750 cites W2118716021 @default.
- W1988718750 cites W2139127225 @default.
- W1988718750 cites W2150765592 @default.
- W1988718750 cites W2160392687 @default.
- W1988718750 cites W2171002179 @default.
- W1988718750 cites W2324186023 @default.
- W1988718750 cites W2343271771 @default.
- W1988718750 cites W2949152083 @default.
- W1988718750 cites W2949154735 @default.
- W1988718750 cites W2949219570 @default.
- W1988718750 cites W2949352806 @default.
- W1988718750 cites W2949444660 @default.
- W1988718750 cites W2949765786 @default.
- W1988718750 cites W2950116792 @default.
- W1988718750 cites W2950445956 @default.
- W1988718750 cites W2951804935 @default.
- W1988718750 cites W2951929582 @default.
- W1988718750 cites W2951968799 @default.
- W1988718750 cites W2953011238 @default.
- W1988718750 cites W2953203249 @default.
- W1988718750 cites W3022813728 @default.
- W1988718750 cites W4229603013 @default.
- W1988718750 cites W4239841441 @default.
- W1988718750 cites W4249305655 @default.
- W1988718750 doi "https://doi.org/10.1021/jo035258x" @default.
- W1988718750 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15104448" @default.
- W1988718750 hasPublicationYear "2004" @default.
- W1988718750 type Work @default.
- W1988718750 sameAs 1988718750 @default.
- W1988718750 citedByCount "58" @default.
- W1988718750 countsByYear W19887187502012 @default.
- W1988718750 countsByYear W19887187502013 @default.
- W1988718750 countsByYear W19887187502014 @default.
- W1988718750 countsByYear W19887187502015 @default.
- W1988718750 countsByYear W19887187502016 @default.
- W1988718750 countsByYear W19887187502017 @default.
- W1988718750 countsByYear W19887187502020 @default.
- W1988718750 countsByYear W19887187502021 @default.
- W1988718750 countsByYear W19887187502023 @default.
- W1988718750 crossrefType "journal-article" @default.
- W1988718750 hasAuthorship W1988718750A5049719312 @default.
- W1988718750 hasAuthorship W1988718750A5059031550 @default.
- W1988718750 hasConcept C146686406 @default.
- W1988718750 hasConcept C161790260 @default.
- W1988718750 hasConcept C178790620 @default.
- W1988718750 hasConcept C181647583 @default.
- W1988718750 hasConcept C183882617 @default.
- W1988718750 hasConcept C185592680 @default.
- W1988718750 hasConcept C2776920199 @default.
- W1988718750 hasConcept C2777667214 @default.
- W1988718750 hasConcept C2777672777 @default.
- W1988718750 hasConcept C2779768532 @default.
- W1988718750 hasConcept C2780591741 @default.
- W1988718750 hasConcept C2780997848 @default.
- W1988718750 hasConcept C35753019 @default.
- W1988718750 hasConcept C71240020 @default.
- W1988718750 hasConceptScore W1988718750C146686406 @default.
- W1988718750 hasConceptScore W1988718750C161790260 @default.
- W1988718750 hasConceptScore W1988718750C178790620 @default.
- W1988718750 hasConceptScore W1988718750C181647583 @default.
- W1988718750 hasConceptScore W1988718750C183882617 @default.
- W1988718750 hasConceptScore W1988718750C185592680 @default.
- W1988718750 hasConceptScore W1988718750C2776920199 @default.
- W1988718750 hasConceptScore W1988718750C2777667214 @default.