Matches in SemOpenAlex for { <https://semopenalex.org/work/W2150244865> ?p ?o ?g. }
- W2150244865 endingPage "2602" @default.
- W2150244865 startingPage "2594" @default.
- W2150244865 abstract "The new (22R,23S,25R)-3β,16β,26-triacetoxy-cholest-5-ene-22,23-diol (11a) was synthesized from diosgenin (3) through a synthetic route based on chemoselective RuO4 oxidation of (25R)-3β,16β-diacetoxy-23-ethyl-231,26-epoxycholesta-5,23(231)-dien-22-one (9) that afforded (20S,25R)-3β,16β,26-triacetoxycholest-5-ene-22,23-dione (10) which was stereoselectively reduced using NaBH4. Compound 9 was obtained from the known isomeric 22,26-epoxycholest-5-ene steroidal skeleton 8b by treatment with p-TsOH in toluene, amberlyst-15 or directly from diosgenin by treatment with BF3·OEt2/Ac2O. Chemoselective reduction of the 23-keto group of 10, was attained using NaBH4/ZnCl2 at −70 °C to give 23S-14. The NMR spectra of all compounds were unambiguously assigned based on one and two dimensional experiments and the C-22 and C-23 stereochemistry in the diacetate derivative 11b, as well as the structure of epoxycholestene 9 were further established by X-ray diffraction analyses. The new route for the functionalization of the side chain of diosgenin can find application in the synthesis of norbrassinosteroid analogues." @default.
- W2150244865 created "2016-06-24" @default.
- W2150244865 creator A5001009717 @default.
- W2150244865 creator A5006121547 @default.
- W2150244865 creator A5021417969 @default.
- W2150244865 creator A5026443615 @default.
- W2150244865 creator A5028214123 @default.
- W2150244865 creator A5037424191 @default.
- W2150244865 creator A5072501073 @default.
- W2150244865 creator A5075504583 @default.
- W2150244865 date "2006-03-01" @default.
- W2150244865 modified "2023-10-16" @default.
- W2150244865 title "A new route for the preparation of the 22,23-dioxocholestane side chain from diosgenin and its application to the stereocontrolled construction of the 22R,23S-diol function" @default.
- W2150244865 cites W1965338698 @default.
- W2150244865 cites W1965650139 @default.
- W2150244865 cites W1972568914 @default.
- W2150244865 cites W1975740630 @default.
- W2150244865 cites W1977181129 @default.
- W2150244865 cites W1977437351 @default.
- W2150244865 cites W1978811296 @default.
- W2150244865 cites W1979708784 @default.
- W2150244865 cites W1981188316 @default.
- W2150244865 cites W1991324282 @default.
- W2150244865 cites W1998171613 @default.
- W2150244865 cites W2003788631 @default.
- W2150244865 cites W2006311961 @default.
- W2150244865 cites W2006629928 @default.
- W2150244865 cites W2007554750 @default.
- W2150244865 cites W2007827871 @default.
- W2150244865 cites W2015321378 @default.
- W2150244865 cites W2019001450 @default.
- W2150244865 cites W2019069326 @default.
- W2150244865 cites W2023695570 @default.
- W2150244865 cites W2029461162 @default.
- W2150244865 cites W2035333328 @default.
- W2150244865 cites W2042435673 @default.
- W2150244865 cites W2042818850 @default.
- W2150244865 cites W2065934234 @default.
- W2150244865 cites W2069096763 @default.
- W2150244865 cites W2072091833 @default.
- W2150244865 cites W2074371704 @default.
- W2150244865 cites W2092142172 @default.
- W2150244865 cites W2092569430 @default.
- W2150244865 cites W2100235508 @default.
- W2150244865 cites W2115813782 @default.
- W2150244865 cites W2133307478 @default.
- W2150244865 cites W2155327755 @default.
- W2150244865 cites W2159027463 @default.
- W2150244865 cites W2241122914 @default.
- W2150244865 cites W2317239216 @default.
- W2150244865 cites W2321089830 @default.
- W2150244865 cites W2325264137 @default.
- W2150244865 cites W2326930870 @default.
- W2150244865 doi "https://doi.org/10.1016/j.tet.2005.12.036" @default.
- W2150244865 hasPublicationYear "2006" @default.
- W2150244865 type Work @default.
- W2150244865 sameAs 2150244865 @default.
- W2150244865 citedByCount "25" @default.
- W2150244865 countsByYear W21502448652012 @default.
- W2150244865 countsByYear W21502448652013 @default.
- W2150244865 countsByYear W21502448652014 @default.
- W2150244865 countsByYear W21502448652015 @default.
- W2150244865 countsByYear W21502448652016 @default.
- W2150244865 countsByYear W21502448652017 @default.
- W2150244865 countsByYear W21502448652019 @default.
- W2150244865 countsByYear W21502448652021 @default.
- W2150244865 countsByYear W21502448652022 @default.
- W2150244865 crossrefType "journal-article" @default.
- W2150244865 hasAuthorship W2150244865A5001009717 @default.
- W2150244865 hasAuthorship W2150244865A5006121547 @default.
- W2150244865 hasAuthorship W2150244865A5021417969 @default.
- W2150244865 hasAuthorship W2150244865A5026443615 @default.
- W2150244865 hasAuthorship W2150244865A5028214123 @default.
- W2150244865 hasAuthorship W2150244865A5037424191 @default.
- W2150244865 hasAuthorship W2150244865A5072501073 @default.
- W2150244865 hasAuthorship W2150244865A5075504583 @default.
- W2150244865 hasConcept C106159729 @default.
- W2150244865 hasConcept C111771559 @default.
- W2150244865 hasConcept C162324750 @default.
- W2150244865 hasConcept C178790620 @default.
- W2150244865 hasConcept C185592680 @default.
- W2150244865 hasConcept C203130289 @default.
- W2150244865 hasConcept C204921945 @default.
- W2150244865 hasConcept C2776601336 @default.
- W2150244865 hasConcept C2779515768 @default.
- W2150244865 hasConcept C521977710 @default.
- W2150244865 hasConcept C71240020 @default.
- W2150244865 hasConceptScore W2150244865C106159729 @default.
- W2150244865 hasConceptScore W2150244865C111771559 @default.
- W2150244865 hasConceptScore W2150244865C162324750 @default.
- W2150244865 hasConceptScore W2150244865C178790620 @default.
- W2150244865 hasConceptScore W2150244865C185592680 @default.
- W2150244865 hasConceptScore W2150244865C203130289 @default.
- W2150244865 hasConceptScore W2150244865C204921945 @default.
- W2150244865 hasConceptScore W2150244865C2776601336 @default.
- W2150244865 hasConceptScore W2150244865C2779515768 @default.
- W2150244865 hasConceptScore W2150244865C521977710 @default.
- W2150244865 hasConceptScore W2150244865C71240020 @default.