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First enantioselectiv synthesis of (+)-tran-195A with a RRM and a zirconium-mediated Negishi-coupling as key steps.

Decahydroquinoline trans-195A was first isolated as a trace compound from neotropical dendrobatid frogs of the genus Epipedobates bassleri. These amphibian alkaloids have proven to be non-competitive blockers of nicotinic receptor channels and are thus interesting agents for biomedical research. The decahydrochinoline structure of trans-195A has been constructed by ring-rearrangement-metathesis (RRM) and zirconium-mediated coupling of the resulting double bonds as key steps. The required enantiopure metathesis precursor was synthesized by Mitsunobu reaction of a chiral amine, accesible by double copper-catalyzed epoxide ring-opening of (-)-epichlorhydrine with Grignard reagents and subsequent substitution, and cyclohexenol, which was obtained with 99% ee via CBS reduction.

By comparison of the synthesized (+)-enantiomer with the isolated substance, the tentative absolute configuration of naturally occuring trans-195A was determined.

N. Holub, J. Neidhoefer, S. Blechert, Total Synthesis of (+)-trans-195A Org. Lett. 2005, 7, 1227-1229. [DOI]

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