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• W2076753488 abstract "The absolute configuration of gymnocin-B has been determined to be (S)-10 and (S)-37. Three challenges toward the configurational assignment of this largest of the polyether marine toxin include (i) introduction of p-(meso-triphenylporphyrin)-cinnamate group (TPPcinnamate) on sterically hindered 10-, 37-hydroxyls under mild conditions, (ii) conformational analysis in the presence of TPPcinnamates at C-10 and C-37 positions on the flexible seven-membered rings embodied in a large polyether ladder-like scaffold structure, and (iii) determination of the chirality at C-10 and C-37 on the basis of porphyrin/porphyrin circular dichroism exciton-coupled interaction over a large distance. The experimentally obtained positive exciton couplet by CD and FDCD of the bis-TPPcin derivative of gymnocin-B is in good agreement with that of theoretically calculated CD of the MMFF optimized structures, by employing DeVoe's coupled oscillator approach, thus establishing the full absolute configuration of gymnocin-B." @default.
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• W2076753488 date "2005-06-11" @default.
• W2076753488 modified "2023-10-09" @default.
• W2076753488 title "Three Challenges toward the Assignment of Absolute Configuration of Gymnocin-B" @default.
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• W2076753488 doi "https://doi.org/10.1021/ja0512677" @default.
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