The total synthesis of (+/-)-2- O-methylneovibsanin H was achieved in 12 steps. An acid-catalyzed, one-pot, four-step cascade reaction was key to the concise total synthesis, lending support to the proposed biosynthesis.
Cubane can be considered the ideal internal standard for reactions observed by NMR, due to an almost complete benign reactivity and uniquely reliable 1H and 13C NMR resonances, in wide variety of deuterated solvents.
(+/-)-4,5-Bis-epi-neovibsanin A and B were synthesized in 12 steps. The acid-catalyzed, one-pot, five-step cascade reaction was central toward the formation of the tricyclic core. The two diastereomers of natural neovibsanin A and B acted as desirable derivatives for structure-activity relationship studies to probe neurotrophic activity. Both (+/-)-4,5-bis-epi-neovibsanin A and B strongly potentiate neurite outgrowth in NGF-stimulated PC12 cells. Furthermore, the tricyclic core appears to be largely responsible for promoting a biological response.
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