Z-Pelletierine

Pelletierine, CgHisON (185, 205) as isolated from the bark is the dl-modification although it is not certain that this is the form in which it occurs in the plant since the isolation of the l-form and its facile racemiza-tion have been reported (216). A similar observation made concerning 1-pelletierine obtained from the dZ-base by resolution (217) confirms the last statement. However, the optical activity of Tanret s Z-pelletierine is much greater than that reported for the resolved base. Hess and coworkers (217, 218) claim that they never succeeded in detecting optical activity in the bases either before or after distillation. 

In view of the fact that pelletierine and isopelletierine are identical it has been proposed that the name isopelletierine be dropped and that the name pelletierine be used to represent (2-piperidyl)-2-propanone and iV-methylpelletierine to represent the corresponding iV -methyl compound (12). Tanret s pelletierine is thus Z-pelletierine Tanret s isopelletierine, Hess s racemic isopelletierine, and Hess s pelletierine are cZZ-pelletierine. A detailed review of the chemistry of pelletierine has appeared (13). 

Z-Pelletierine has been shown to possess the It configuration (II) at the asymmetric center (14). (— )-Sedridine, known to have the B configuration at the asymmetric center in the piperidine ring, furnishes iZ-( — )-pelletierine when oxidized with chromic acid in aqueous acetic acid. (-I-)-Sedridine gives 5-(- -)-pelletierine on oxidation (14). The method of resolution of racemic pelletierine through salts with the 6,6 -dinitrophenyl-2,2 -dicarboxylic acids (15) has been improved (16). 

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