FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2058668626> ?p ?o ?g. }

• W2058668626 endingPage "8066" @default.
• W2058668626 startingPage "8056" @default.
• W2058668626 abstract "Abstract A solid‐phase method for the synthesis of tri‐, tetra‐, and pentacyclic compounds containing tetrahydro‐β‐carboline, tetrahydroisoquinoline or analogous scaffolds is presented. The reaction proceeds with high stereoselectivity through an intermediate N ‐carbamyliminium ion that exclusively converts into Pictet–Spengler‐type products with a variety of C‐nucleophiles. Amino aldehydes masked with 3‐Boc‐(1,3)‐oxazinane (Box) have been synthesized from amino acids, amino alcohols, or 2‐nitro benzaldehydes. The amino moiety of these masked aldehydes has been converted into pentafluorophenyl carbamate to serve as a urea precursor. The building blocks were incorporated at the N ‐terminal of a resin‐supported dipeptide through urea formation. Subsequent treatment with acid liberated the aldehyde quantitatively. A penultimate tryptophan residue gave rise, under the acetic conditions, to a spontaneous intramolecular Pictet–Spengler reaction with the liberated aldehyde. The reaction proceeded with a high degree of stereoselectivity affording tetrahydro‐β‐carbolines with a de ( de =diastereomeric excess) above 95 % and purity in the range of 90–99 %. This reaction has been extended to a range of other aromatic C‐nucleophiles, including substituted indoles, benzenes, pyrene, furan, thiophenes, and benzothiophene with comparable stereoselectivity and purity. Prolonged exposure of the benzaldehyde‐derived Pictet–Spengler products to strong acid and air lead to quantitative auto‐oxidation which yielded compounds with a 3,4‐dihydro‐β‐carboline, a 3,4‐dihydroisoquinoline, or a similar core structure." @default.
• W2058668626 created "2016-06-24" @default.
• W2058668626 creator A5043993541 @default.
• W2058668626 creator A5062868348 @default.
• W2058668626 creator A5091170218 @default.
• W2058668626 date "2006-10-19" @default.
• W2058668626 modified "2023-10-17" @default.
• W2058668626 title "Solid-Phase Synthesis of Tetrahydro-β-carbolines and Tetrahydroisoquinolines by Stereoselective IntramolecularN-Carbamyliminium Pictet–Spengler Reactions" @default.
• W2058668626 cites W1977447667 @default.
• W2058668626 cites W1980343971 @default.
• W2058668626 cites W1988184759 @default.
• W2058668626 cites W1989309374 @default.
• W2058668626 cites W1990998145 @default.
• W2058668626 cites W1993491755 @default.
• W2058668626 cites W2008423708 @default.
• W2058668626 cites W2014196024 @default.
• W2058668626 cites W2020354662 @default.
• W2058668626 cites W2021005940 @default.
• W2058668626 cites W2022864303 @default.
• W2058668626 cites W2025683965 @default.
• W2058668626 cites W2027059832 @default.
• W2058668626 cites W2028770848 @default.
• W2058668626 cites W2038230240 @default.
• W2058668626 cites W2047400615 @default.
• W2058668626 cites W2051074466 @default.
• W2058668626 cites W2055966902 @default.
• W2058668626 cites W2059680068 @default.
• W2058668626 cites W2063709439 @default.
• W2058668626 cites W2065463005 @default.
• W2058668626 cites W2066792399 @default.
• W2058668626 cites W2067294395 @default.
• W2058668626 cites W2071168359 @default.
• W2058668626 cites W2071359038 @default.
• W2058668626 cites W2076703066 @default.
• W2058668626 cites W2077567873 @default.
• W2058668626 cites W2084299952 @default.
• W2058668626 cites W2084475131 @default.
• W2058668626 cites W2086278227 @default.
• W2058668626 cites W2110478240 @default.
• W2058668626 cites W2113489836 @default.
• W2058668626 cites W2118417270 @default.
• W2058668626 cites W2132070963 @default.
• W2058668626 cites W2149415057 @default.
• W2058668626 cites W2344640911 @default.
• W2058668626 cites W2950284647 @default.
• W2058668626 cites W2951961610 @default.
• W2058668626 cites W4230382175 @default.
• W2058668626 cites W4237751738 @default.
• W2058668626 doi "https://doi.org/10.1002/chem.200600138" @default.
• W2058668626 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16881029" @default.
• W2058668626 hasPublicationYear "2006" @default.
• W2058668626 type Work @default.
• W2058668626 sameAs 2058668626 @default.
• W2058668626 citedByCount "46" @default.
• W2058668626 countsByYear W20586686262012 @default.
• W2058668626 countsByYear W20586686262013 @default.
• W2058668626 countsByYear W20586686262015 @default.
• W2058668626 countsByYear W20586686262016 @default.
• W2058668626 countsByYear W20586686262017 @default.
• W2058668626 countsByYear W20586686262018 @default.
• W2058668626 countsByYear W20586686262019 @default.
• W2058668626 countsByYear W20586686262020 @default.
• W2058668626 countsByYear W20586686262021 @default.
• W2058668626 countsByYear W20586686262023 @default.
• W2058668626 crossrefType "journal-article" @default.
• W2058668626 hasAuthorship W2058668626A5043993541 @default.
• W2058668626 hasAuthorship W2058668626A5062868348 @default.
• W2058668626 hasAuthorship W2058668626A5091170218 @default.
• W2058668626 hasConcept C138716334 @default.
• W2058668626 hasConcept C161790260 @default.
• W2058668626 hasConcept C178790620 @default.
• W2058668626 hasConcept C178907741 @default.
• W2058668626 hasConcept C181647583 @default.
• W2058668626 hasConcept C185592680 @default.
• W2058668626 hasConcept C2776568683 @default.
• W2058668626 hasConcept C2779692420 @default.
• W2058668626 hasConcept C2779825165 @default.
• W2058668626 hasConcept C515207424 @default.
• W2058668626 hasConcept C55493867 @default.
• W2058668626 hasConceptScore W2058668626C138716334 @default.
• W2058668626 hasConceptScore W2058668626C161790260 @default.
• W2058668626 hasConceptScore W2058668626C178790620 @default.
• W2058668626 hasConceptScore W2058668626C178907741 @default.
• W2058668626 hasConceptScore W2058668626C181647583 @default.
• W2058668626 hasConceptScore W2058668626C185592680 @default.
• W2058668626 hasConceptScore W2058668626C2776568683 @default.
• W2058668626 hasConceptScore W2058668626C2779692420 @default.
• W2058668626 hasConceptScore W2058668626C2779825165 @default.
• W2058668626 hasConceptScore W2058668626C515207424 @default.
• W2058668626 hasConceptScore W2058668626C55493867 @default.
• W2058668626 hasIssue "31" @default.
• W2058668626 hasLocation W20586686261 @default.
• W2058668626 hasLocation W20586686262 @default.
• W2058668626 hasOpenAccess W2058668626 @default.
• W2058668626 hasPrimaryLocation W20586686261 @default.
• W2058668626 hasRelatedWork W1533372989 @default.
• W2058668626 hasRelatedWork W1969295444 @default.
• W2058668626 hasRelatedWork W2010820983 @default.

• next