Abstract
Schemes for the degradation of narcotine (III) are devised which allow unambiguous isolation of labelled atoms from the alkaloid isolated from Papaver somniferum plants fed with a variety of precursors, both singly and multiply-labelled. It is shown in this way that the biosynthesis involves combination of two Ar–C–C units, derivable in the living plant from tyrosine, to generate norlaudanosoline (VII). O-, and N-Methylation from the S-methyl group of methionine then yields reticuline [as (X)], the (+)-isomer of which (X) undergoes oxidative ring-closure to yield (–)-scoulerine (XLII). Further oxidative attack at positions 1, 8, and 13 are then involved in the final steps leading to narcotine. The results from 3H, 14C-labelling experiments are in agreement with stereospecific attack at position 13.The synthesis and resolution of labelled 1-benzylisoquinolines and scoulerine are described.
Published Version
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