Demethyl-tubulosine

Alangium lamarckii Lour. dl-Anabasine, cephaeline, emetine, psychotrine, tubulosine, ankorine isotubulosine, demethyl-tubulosine, demethylpsychotrin, alangicine, deoxytubulosine, alangimarckine, alamarchine, demethylcephaeline.33 ... 

A key component required for the synthesis of an antitumor alkaloid (73, 9-demethyl-tubulosine) is obtained in 82% yield via amidation of heterocyclic acid 71 and 5-benzyloxy-tryptamine (72).28 9-Demethyltubulosine increases the survival time of mice infected with leukemia L1210 or P388. 

Since the previous racemic and chiral syntheses of deoxytubulosine (31) were reviewed (1), Brown and Jones (68) have reported the synthesis of ( )-deoxytubulosine [( )-31] and its I -epimer (129) by Pictet-Spengler reaction of ( )-protoemetine [( )-6] (Section III,A) with tryptamine. For a study on the biosynthesis of tubulosine (26), Bhakuni etal. (114) prepared didemethyl-deoxytubulosine (131) from deoxytubulosine (31) by demethyl-ation with HBr in AcOH. Both 131 and 31 were then tritiated in an acid-catalyzed exchange reaction to furnish [aryl- H]didemethyl-deoxytubulo-sine and [aryl- H]deoxytubulosine, respectively. 

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