Abstract (+)‐Sedridine fromSedum acreL. is shown to be (2S)‐1‐[(2′S)‐2′‐piperidyl]‐propan‐2‐ol. Oxidation of unnatural (‐)‐sedridine yieldedD‐pipecolic acid, from which follows the absolute configuration of the piperidine asymmetric centre. Oxidation of unnatural (+)‐pelletierine sulfate gaveL‐pipecolic acid. This also confirms a previous deduction of the absolute configuration of (‐)‐pelletierine fromPunica granatumL.; this is R‐1‐(2‐piperidyl)propan‐2‐one. Racemic sedridine and allosedridine were condensed withp‐substituted benzaldehydes to 1‐(4‐substituted‐phenyl)‐3‐methylhexahydro‐1H,3H‐pyrido‐[1,2‐c]oxazines. The relative configurations followed from conformational analysis and proton magnetic resonance spectra: sedridine isthreoidand allosedridine iserythroid.
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Beyerman et al. (1965) studied this question.
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