Tetrahedron p. 3175 - 3182 (1981)
Update date:2022-08-18
Topics:
Bhakuni, Dewan S.
Jain, Sudha
Incorporation of tyrosine, dopa, dopamine, 4-hydroxyphenylpyruvic acid, (+/-)-, norcoclaurine-1-carboxylic acid, -norcoclaurine, -coclaurine, and -N-methylcoclaurine into N-methylcrotsparine, N-methylcrotsparinine and N-methylsparsiflorine in Croton sparsiflorus Morong has been studied.The evidence supports the direct oxidative coupling of (+)-, and (-)-N-methylcoclaurines to give N-methylcrotsparine and N-methylcrotsparinine, respectively.Tracer experiment show that N-methylcrotsparine undergoes dienone-phenol rearrangement to give N-methylsparsiflorine.A doublelabelling experiment with (+/-)-N<14C>methyl<1-3H>coclaurine demonstrated that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion.The intermediacy of norcoclaurine-1-carboxylic acid and specific incorporation of dehydro-N-methylcoclaurinium salt into the bases have been demonstrated.
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(1979)