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An advanced intermediate for the heterocyclic aminal core of zoanthamine/norzoanthamine alkaloids was prepared in an enantio and stereoselective manner. Contiguous quaternary chiral centers were selectively constructed utilizing a stereoselective cuprate addition to the readily available (+)-Wieland-Miescher ketone.
Stereocontrolled construction of the fully functionalized heterocyclic aminal core (CDEFG ring) of the zoanthamine and norzoanthamine family was successfully accomplished from the monocyclic ketoacid which was prepared from (+)-Wieland-Miescher ketone and D-glutamic acid.
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