FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2896916499> ?p ?o ?g. }

• W2896916499 endingPage "541" @default.
• W2896916499 startingPage "535" @default.
• W2896916499 abstract "(-)-Naltrexone, an opioid antagonist used extensively for the management of drug abuse, is derived from naturally occurring opioids. Herein, we report the first asymmetric synthesis of (-)-naltrexone that does not proceed through thebaine. The synthesis starts with simple, achiral precursors with catalytic enantioselective Sharpless dihydroxylation employed to introduce the stereogenic centers. A Rh(i)-catalyzed C-H alkenylation and torquoselective electrocyclization cascade provides the hexahydro isoquinoline bicyclic framework that serves as the precursor to the morphinan core. The acidic conditions used for Grewe cyclization not only provide the morphinan framework, but also cause a hydride shift resulting in the introduction of the C-6 oxo functionality present in (-)-naltrexone. The C-14 hydroxyl group is installed by an efficient two-step sequence of Pd-mediated ketone to enone dehydrogenation followed by C-H allylic oxidation using Cu(ii) and O2, a method that has not previously been reported either for the synthesis or semi-synthesis of opioids. The longest linear sequence is 17 steps, and because the stereogenic centers in the product rely on Sharpless asymmetric dihydroxylation, the route could be used to access either enantiomer of the natural product, which have disparate biological activities. The route also may be applicable to the preparation of opioid derivatives that could not be easily prepared from the more fully elaborated and densely functionalized opioid natural products that have traditionally served as the starting inputs." @default.
• W2896916499 created "2018-10-26" @default.
• W2896916499 creator A5012406363 @default.
• W2896916499 creator A5042297663 @default.
• W2896916499 creator A5053930897 @default.
• W2896916499 date "2019-01-01" @default.
• W2896916499 modified "2023-10-01" @default.
• W2896916499 title "Asymmetric synthesis of (−)-naltrexone" @default.
• W2896916499 cites W101291630 @default.
• W2896916499 cites W1963739535 @default.
• W2896916499 cites W1965070188 @default.
• W2896916499 cites W1969336064 @default.
• W2896916499 cites W1973355981 @default.
• W2896916499 cites W1976718593 @default.
• W2896916499 cites W1977855155 @default.
• W2896916499 cites W1985958610 @default.
• W2896916499 cites W1988311914 @default.
• W2896916499 cites W1988353431 @default.
• W2896916499 cites W1988551034 @default.
• W2896916499 cites W1991421016 @default.
• W2896916499 cites W2004398127 @default.
• W2896916499 cites W2004652298 @default.
• W2896916499 cites W2005434980 @default.
• W2896916499 cites W2006996850 @default.
• W2896916499 cites W2007569009 @default.
• W2896916499 cites W2009217186 @default.
• W2896916499 cites W2009409799 @default.
• W2896916499 cites W2014242022 @default.
• W2896916499 cites W2014712150 @default.
• W2896916499 cites W2016329324 @default.
• W2896916499 cites W2028838717 @default.
• W2896916499 cites W2028850775 @default.
• W2896916499 cites W2029748062 @default.
• W2896916499 cites W2029993440 @default.
• W2896916499 cites W2030350011 @default.
• W2896916499 cites W2031582639 @default.
• W2896916499 cites W2034523575 @default.
• W2896916499 cites W2038854479 @default.
• W2896916499 cites W2039614696 @default.
• W2896916499 cites W2042544761 @default.
• W2896916499 cites W2042712213 @default.
• W2896916499 cites W2060734995 @default.
• W2896916499 cites W2061500293 @default.
• W2896916499 cites W2063756325 @default.
• W2896916499 cites W2068610845 @default.
• W2896916499 cites W2083526120 @default.
• W2896916499 cites W2083532627 @default.
• W2896916499 cites W2086925748 @default.
• W2896916499 cites W2087484668 @default.
• W2896916499 cites W2091023270 @default.
• W2896916499 cites W2093269166 @default.
• W2896916499 cites W2093384490 @default.
• W2896916499 cites W2108163830 @default.
• W2896916499 cites W2108774921 @default.
• W2896916499 cites W2114094827 @default.
• W2896916499 cites W2117864656 @default.
• W2896916499 cites W2120400560 @default.
• W2896916499 cites W2127719167 @default.
• W2896916499 cites W2135088205 @default.
• W2896916499 cites W2144441791 @default.
• W2896916499 cites W2154822745 @default.
• W2896916499 cites W2157001985 @default.
• W2896916499 cites W2158834330 @default.
• W2896916499 cites W2159634309 @default.
• W2896916499 cites W2161409970 @default.
• W2896916499 cites W2165763573 @default.
• W2896916499 cites W2188872902 @default.
• W2896916499 cites W2317758222 @default.
• W2896916499 cites W2326925635 @default.
• W2896916499 cites W2404283831 @default.
• W2896916499 cites W2412243856 @default.
• W2896916499 cites W2476204511 @default.
• W2896916499 cites W2524552526 @default.
• W2896916499 cites W2752311515 @default.
• W2896916499 cites W2782672337 @default.
• W2896916499 cites W2949512038 @default.
• W2896916499 cites W2950019430 @default.
• W2896916499 cites W2950454782 @default.
• W2896916499 cites W2951054370 @default.
• W2896916499 cites W4235133912 @default.
• W2896916499 cites W4242505774 @default.
• W2896916499 doi "https://doi.org/10.1039/c8sc03748e" @default.
• W2896916499 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6326069" @default.
• W2896916499 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30713650" @default.
• W2896916499 hasPublicationYear "2019" @default.
• W2896916499 type Work @default.
• W2896916499 sameAs 2896916499 @default.
• W2896916499 citedByCount "16" @default.
• W2896916499 countsByYear W28969164992019 @default.
• W2896916499 countsByYear W28969164992020 @default.
• W2896916499 countsByYear W28969164992021 @default.
• W2896916499 countsByYear W28969164992022 @default.
• W2896916499 countsByYear W28969164992023 @default.
• W2896916499 crossrefType "journal-article" @default.
• W2896916499 hasAuthorship W2896916499A5012406363 @default.
• W2896916499 hasAuthorship W2896916499A5042297663 @default.
• W2896916499 hasAuthorship W2896916499A5053930897 @default.
• W2896916499 hasBestOaLocation W28969164991 @default.

• next