Matches in SemOpenAlex for { <https://semopenalex.org/work/W2093926858> ?p ?o ?g. }
- W2093926858 endingPage "988" @default.
- W2093926858 startingPage "981" @default.
- W2093926858 abstract "Trienes and dienynes containing one electron-deficient double bond were shown to undergo regio- and stereoselective oxidative cyclization in the presence of permanganate ion to afford 2,5-bis-hydroxyalkyltetrahydrofurans (THF diols). The THF diols produced retained either alkene or alkyne functionalities, which provided convenient handles for the metal oxo-mediated introduction of an adjacent THF ring with overall control of relative and absolute stereochemistry. Adjacent bis-THFs possessing threo-cis-threo-trans-erythro, threo-cis-threo-trans-threo, threo-cis-threo-cis-erythro, threo-cis-erythro-cis-threo, or threo-cis-erythro-trans-threo relationships were synthesized by appropriate selection of alkene geometry and methodology for the closure of the second ring. The threo-cis-threo-cis-erythro stereochemical arrangement is embodied within the bis-THF core units of a number of Annonaceous acetogenins including membrarollin, while trilobacin has a threo-cis-erythro-trans-threo configured core. As an application of the selective oxidative cyclization approach, a total synthesis of membrarollin was completed in 17 linear steps from dodecyne. The C21,C22 double epimer of membrarollin was also synthesized in 15 linear steps and without recourse to the use of hydroxyl group protection." @default.
- W2093926858 created "2016-06-24" @default.
- W2093926858 creator A5000859953 @default.
- W2093926858 creator A5047211933 @default.
- W2093926858 creator A5053198446 @default.
- W2093926858 creator A5061493169 @default.
- W2093926858 creator A5079061934 @default.
- W2093926858 creator A5088931460 @default.
- W2093926858 date "2009-01-08" @default.
- W2093926858 modified "2023-10-16" @default.
- W2093926858 title "Oxidative Cyclization Reactions of Trienes and Dienynes: Total Synthesis of Membrarollin" @default.
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