The 3-arylpyrrolidine alkaloid synthon : A formal total synthesis of Cepharamine (cas 15444-26-5) utilizing an endocyclic enamine☆

Add time:08/16/2019    Source:sciencedirect.com

A formal total synthesis of the hasubanonine alkaloid Cepharamine (cas 15444-26-5) (3b) from 7,8-dimethoxy-2- tetralone has been accomplished. A key intermediate in the synthesis was 3-methyl-1.2.4.5-tetrahydrobenz[e]indole 4a which was prepared by a one step ring expansion reaction of cyclopropyl ketone 8b effected by methylamine. The annelation of 4a with methyl vinyl ketone yielded aminoketone 5a which possesses the tetracyclic skeleton characteristic of the hasubanonine alkaloid group. The oxidation of 5a to 5e. which was reported to have been converted to cepharamine, completed the formal total synthesis of that alkaloid. The foregoing transformations and others related to than have also been carried out in the analogous desmethoxy series of compounds beginning with β-tetralone, 8d.

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