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- W2136727502 abstract "The first total synthesis of (+)-astrophylline (2) has been achieved, starting from readily available enantiomerically pure (+)-(1R,4S)-4-hydroxycyclopent-2-enyl acetate (11). A novel ruthenium-catalyzed ring-closing ring-opening ring-closing metathesis of carbocyclic olefins of general type 5 was the key step, providing the stereochemically well-defined bis-piperidyl skeleton of the target molecule. A [2,3]-Wittig-Still rearrangement of 9 was also employed as the critical transformation in the stereocontrolled generation of the 1,2-trans configuration of the cyclopentene intermediate 6c. Our early synthetic efforts toward 1,2-trans cyclopentene derivatives of type 6, as well as the synthetic pathway to an optimized 13-step total synthesis of 2 (12% overall yield), are reported." @default.
- W2136727502 created "2016-06-24" @default.
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- W2136727502 date "2003-03-07" @default.
- W2136727502 modified "2023-10-14" @default.
- W2136727502 title "Total Synthesis of (+)-Astrophylline" @default.
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- W2136727502 doi "https://doi.org/10.1021/jo026803h" @default.
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