Specifically ring-labelled (±)-pelletierine

Abstract

A synthesis of 2-14C- and of 6-14C-(±)-pelletierine and (±)-α-phenacylpiperidine is described, starting from 2-14C- and 6-14C-(±)-lysine, respectively.

Biosynthesis of lycopodine. Incorporation of Δ1-piperideine and of pelletierine

“…The results of these degradations are presented in Tables 2, 3, and 4. As anticipated, A'-piperideine (4) serves as a specific precursor of lycopodine. Consistent with the established evidence (5,6) that the position of the double bond in A'-piperideine is fixed, the patterns of distribution in lycopodine of activity from 2-14C-and from 6-14C-A'-piperideine differ ( Table 2). Half of the radioactivity of the lycopodine, derived from 2-14C-A'-piperideine, was recovered from C-5 (benzoic acid), whereas C-9 (formic acid) was devoid of activity.…”

“…In the present investigation we have examined the status in the biosynthesis of lycopodine of two further intermediates of the hypothetical sequence, A'-piperideine (4) and pelletierine (5).…”

“…A solution of A'-pi~eriheine hydrochloride, prepared from inactive DL-lysine monohvdrochloride (0.5 mmole) (5) , , , was then addkd dropwise, over 24 h, and'(*)-pelletierine hydrochloride, total activity 0.034 mCi (7% yield), was isolated and purified by the method reported previously (5). Final purification was achieved by sublimation at 140" and 3 x mm.…”

The biosynthesis of the Lythraceae alkaloids. I. The lysine-derived fragment

“…[7][8][9][10], and whose side chain originates from acetate (1 1-13). Biogenetically modelled syntheses of pelletierine have been reported (14). Manilich condensation of pelletierine with a C6-C, unit, isovanillin, a reaction which has been employed in biomimetic synthesis (1 5-1 7), yields the phenylquinolizidinone (6).…”

Biosynthesis of Lobinaline

“…11) was prepared from [6-14C]-DL-lysine (Commissariat A 1'~nergie Atomique, France) by the method described in an earlier paper (12).…”