Matches in SemOpenAlex for { <https://semopenalex.org/work/W2000787095> ?p ?o ?g. }
Showing items 1 to 78 of
78
with 100 items per page.
- W2000787095 endingPage "4251" @default.
- W2000787095 startingPage "4247" @default.
- W2000787095 abstract "A bidirectional route to nonracemic C(2)-symmetric bistetrahydrofuran units related to acetogenin natural products was developed starting from the (S,S)-tartrate-derived dialdehyde 3.3. Bis-homologation with the (R)-alpha-OMOM crotylstannane (R)-4.1 in the presence of InCl(3) afforded the anti adduct, diol 4.3. The derived tosylate 4.4, upon treatment with TBAF in THF, underwent sequential TBS cleavage and cyclization to the (R,R,R,R,R,R)-bis-OMOM bistetrahydrofuran 4.7. The epimeric (S,R,R,R,R,S)-bis-OMOM bistetrahydrofuran 4.10 was prepared along similar lines, except that the (R)-alpha-OMOM crotylstannane (R)-4.1 was first converted to the (R)-gamma-isomer (R)-4.2 with BF(3).OEt(2). Subsequent addition of dialdehyde 3.3 led to the diol adduct 4.5, which after tosylation and treatment with TBAF, yielded the bistetrahydrofuran 4.10. By repeating the aforementioned sequences, but starting with the (S)-alpha-OMOM-crotylstannane (S)-4.1, the (S,S,R,R,S,S)- and the (R,S,R,R,S,R)-bistetrahydrofurans 5.5 and 5.8 were prepared. A variation on the foregoing sequence in which the OTBS grouping of the adduct was converted to a mesylate and the OH group was used to effect intramolecular displacement was also examined. Accordingly, adduct ent-5.3 from BF(3)-promoted addition of stannane (R)-4.2 and ent-3.3, the enantiomer of aldehyde 3.3, was acetylated. Cleavage of the TBS ether followed by mesylate formation and then concommitant acetate hydrolysis and cyclization with methanolic Triton B yielded the bis-OMOM bistetrahydrofuran 5.5. An analogous sequence was used to convert adduct 4.3 to ent-4.10. In this case, acetate saponification was effected with methanolic K(2)CO(3), and the resulting diol, 7.4, was cyclized with NaH in THF." @default.
- W2000787095 created "2016-06-24" @default.
- W2000787095 creator A5072851774 @default.
- W2000787095 creator A5085768377 @default.
- W2000787095 date "1996-01-01" @default.
- W2000787095 modified "2023-10-16" @default.
- W2000787095 title "An Efficient Bidirectional Approach to the <i>C</i><sub>2</sub>-Symmetric Stereoisomers of the Bistetrahydrofuran Core of the Acetogenins" @default.
- W2000787095 cites W1974029107 @default.
- W2000787095 cites W1983600006 @default.
- W2000787095 cites W2013713600 @default.
- W2000787095 cites W2038709886 @default.
- W2000787095 cites W2060031647 @default.
- W2000787095 cites W2066906003 @default.
- W2000787095 cites W2158428401 @default.
- W2000787095 cites W2950011569 @default.
- W2000787095 cites W2951183635 @default.
- W2000787095 cites W3004820786 @default.
- W2000787095 doi "https://doi.org/10.1021/jo9603789" @default.
- W2000787095 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11667322" @default.
- W2000787095 hasPublicationYear "1996" @default.
- W2000787095 type Work @default.
- W2000787095 sameAs 2000787095 @default.
- W2000787095 citedByCount "38" @default.
- W2000787095 countsByYear W20007870952012 @default.
- W2000787095 countsByYear W20007870952020 @default.
- W2000787095 crossrefType "journal-article" @default.
- W2000787095 hasAuthorship W2000787095A5072851774 @default.
- W2000787095 hasAuthorship W2000787095A5085768377 @default.
- W2000787095 hasConcept C108204754 @default.
- W2000787095 hasConcept C161790260 @default.
- W2000787095 hasConcept C178790620 @default.
- W2000787095 hasConcept C185592680 @default.
- W2000787095 hasConcept C2777897746 @default.
- W2000787095 hasConcept C2779515768 @default.
- W2000787095 hasConcept C2779825165 @default.
- W2000787095 hasConcept C2780303139 @default.
- W2000787095 hasConcept C2780988704 @default.
- W2000787095 hasConcept C486523 @default.
- W2000787095 hasConcept C556039675 @default.
- W2000787095 hasConcept C71240020 @default.
- W2000787095 hasConcept C71924100 @default.
- W2000787095 hasConcept C75079739 @default.
- W2000787095 hasConceptScore W2000787095C108204754 @default.
- W2000787095 hasConceptScore W2000787095C161790260 @default.
- W2000787095 hasConceptScore W2000787095C178790620 @default.
- W2000787095 hasConceptScore W2000787095C185592680 @default.
- W2000787095 hasConceptScore W2000787095C2777897746 @default.
- W2000787095 hasConceptScore W2000787095C2779515768 @default.
- W2000787095 hasConceptScore W2000787095C2779825165 @default.
- W2000787095 hasConceptScore W2000787095C2780303139 @default.
- W2000787095 hasConceptScore W2000787095C2780988704 @default.
- W2000787095 hasConceptScore W2000787095C486523 @default.
- W2000787095 hasConceptScore W2000787095C556039675 @default.
- W2000787095 hasConceptScore W2000787095C71240020 @default.
- W2000787095 hasConceptScore W2000787095C71924100 @default.
- W2000787095 hasConceptScore W2000787095C75079739 @default.
- W2000787095 hasIssue "13" @default.
- W2000787095 hasLocation W20007870951 @default.
- W2000787095 hasLocation W20007870952 @default.
- W2000787095 hasOpenAccess W2000787095 @default.
- W2000787095 hasPrimaryLocation W20007870951 @default.
- W2000787095 hasRelatedWork W1987183241 @default.
- W2000787095 hasRelatedWork W2002538978 @default.
- W2000787095 hasRelatedWork W2011135912 @default.
- W2000787095 hasRelatedWork W2019054176 @default.
- W2000787095 hasRelatedWork W2054588849 @default.
- W2000787095 hasRelatedWork W2071973567 @default.
- W2000787095 hasRelatedWork W2949305322 @default.
- W2000787095 hasRelatedWork W2949500858 @default.
- W2000787095 hasRelatedWork W2949635873 @default.
- W2000787095 hasRelatedWork W2951057048 @default.
- W2000787095 hasVolume "61" @default.
- W2000787095 isParatext "false" @default.
- W2000787095 isRetracted "false" @default.
- W2000787095 magId "2000787095" @default.
- W2000787095 workType "article" @default.